STYRYL CARBOXYLATE DERIVATIVES

Abstract

Novel Dithiane derivative and methyl cinnamate compounds are provided which exhibit activity for the treatment of immunological diseases, inflammation, obesity, hyperlipidemia, hypertension, neurological diseases, and diabetes.

Claims

1. A methyl cinnamate compound having the following formula ##STR00153##

2. The methyl cinnamate of claim 1 wherein Z is ##STR00154## wherein the IUPAC name of the compound is 4-(1,3-Dithian-2-yl)phenyl cinnamate (RNV-206), or a pharmaceutically acceptable salt thereof.

3. The methyl cinnamate of claim 1 wherein Z is ##STR00155## wherein the IUPAC name of the compound is 4-(1,3-Dithian-2-yl)phenyl cinnamate (RNV-127), or a pharmaceutically acceptable salt thereof.

4. The methyl cinnamate of claim 1 wherein Z is ##STR00156## wherein the IUPAC name of the compound is 4-Bromo-2-(1,3-dithian-2-yl)phenyl cinnamate (RNV-256), or a pharmaceutically acceptable salt thereof.

5. The methyl cinnamate of claim 1 wherein Z is ##STR00157## wherein the IUPAC name of the compound is 4-(1,3-Dithian-2-yl)-2-methoxyphenyl cinnamate (RNV 216), or a pharmaceutically acceptable salt thereof.

6. The methyl cinnamate of claim 1 wherein Z is ##STR00158## wherein the IUPAC name of the compound is 4-(1,3-Dithiolan-2-yl)phenyl cinnamate (RNV 210), or a pharmaceutically acceptable salt thereof.

7. The methyl cinnamate of claim 1 wherein Z is ##STR00159## wherein the IUPAC name of the compound is 4-(1,3-Dithiolan-2-yl)-2-methoxyphenyl cinnamate (RNV 213), or a pharmaceutically acceptable salt thereof.

Description

BRIEF DESCRIPTION OF FIGURES

[0011] FIG. 1A shows that mice treated with compound 1 showed a significant decrease (P<0.0001) by 16% in body weight compared with the Control high fat diet group. FIG. 1B shows that mice treated with compound 1 showed a significant decrease (P<0.0001) by 54% in percent body weight compared with the Control high fat diet group.

[0012] FIG. 2 shows that mice treated with compound 1 showed 15% reduction in fasting blood glucose compared with the control group high fat diet group.

[0013] FIG. 3A shows that group of mice treated with compound 1 showed a significant reduction (P<0.002) by 27% in fasting blood glucose compared with the group of mice maintained on high fat diet. FIG. 3B shows the effect of compound 1 on oral glucose tolerance test at Day 90 when compared with the control group of mice on high fat diet. FIG. 3C shows that the group of mice treated with compound 1 showed a significant decrease (P<0.009) by 28% in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the Control high fat diet group.

[0014] FIG. 4 shows that mice treated with compound 1 showed a 14% decrease in Total Cholesterol and a significant decrease (P<0.01) by 35% in Triglyceride, compared with the Control high fat diet group.

[0015] FIG. 5A shows that at the end of the drug treatment period, the group of mice treated with compound 1 showed a significant (P<0.0001) decrease in body weight by 19%, compared with the high fat diet group. FIG. 5B shows that at the end of the drug treatment period, the group of mice treated with compound 1 showed a 17% decrease in body weight when compared with the control high fat diet group.

[0016] FIG. 6A shows the effect of compound 1 on oral glucose tolerance test FIG. 6B shows that the group of mice treated with compound 1 showed 7% lower fasting blood glucose compared with the Control high fat diet group of mice. FIG. 6B shows that at the end of 120 minutes in the oral glucose tolerance test, the group of mice administered with compound 1 showed a 7% decrease in blood glucose compared with the Control high fat diet group.

[0017] FIG. 7 shows that mice treated with compound 1 showed significant reduction (P<0.0001) by 24% in body weight compared with the untreated group of mice starting from day 6 till the entire duration of the study.

[0018] FIG. 8 shows that mice treated with compound 1 showed significant reduction (P<0.003) by 34% in blood glucose compared with the untreated group of mice starting from day 6 till the entire duration of the study.

[0019] FIG. 9A shows that at the end of the study duration of 30 days, mice treated with compound 1 showed significant reduction (P<0.003) by 34% in blood glucose compared with the untreated group of mice starting from day 6 till the entire duration of the study. FIG. 9B shows that mice treated with compound 1 showed significant reduction by 32% in blood glucose compared with the untreated group of mice.

[0020] FIG. 10A shows that the group of mice administered with compound 1 showed a 24% decrease in Total Cholesterol on day 90 and 34% decrease in Total Cholesterol on day 180 from the control high fat diet group. FIG. 10B shows that the group of mice administered with compound 1 showed a 52% increase on day 90 and 62% increase on day 180 in high density lipoprotein (HDL) from the control high fat diet group. FIG. 10C shows that the group of mice administered with compound 1 showed a 32% decrease in low density lipoprotein (LDL) on day 90 from the control high fat diet group. FIG. 10D shows that the group of mice administered with compound 1 showed a 7% decrease on day 90 and 26% decrease on day 180 in Triglycerides from the control high fat diet group. FIG. 10E shows that the group of mice administered with compound 1 showed a 35% decrease on day 90 and 39% decrease on day 180 in blood glucose from the control high fat diet group.

[0021] FIG. 11A shows that the group of rats treated with compound 1 showed a significant (P<0.002) decrease by 11% in fasting blood glucose than the vehicle group of rats on day 30 and FIG. 11B shows a decrease by 9% on day 60, compared with the Control group of rats.

[0022] FIG. 12 shows that rats treated with compound 1 showed 10% decrease in systolic blood pressure and a 9% decrease in diastolic blood pressure, compared with the control group of rats.

[0023] FIG. 13 shows that rats administered with compound 1 showed a 31% decrease in HOMA IR from the group of Control rats.

[0024] FIG. 14A shows that the group of hamsters administered with compound 1 showed a significant (P<0.03) reduction by 19% blood glucose, compared with the Control group of high fructose fed hamsters. Triglycerides were then measured in the plasma of the fasted hamsters.

[0025] FIG. 14B shows that the group of hamsters treated with compound 1 showed a significant (p<0.0002) decrease by 55% in Triglycerides, compared with the Control group of high fructose fed hamsters.

[0026] FIG. 15 shows that hamsters administered with compound 1 showed a 39% decrease in Total Cholesterol (FIG. 15A), a 35% increase in high-density lipoproteins (HDL) (FIG. 15B), a 34% decrease in low-density lipoproteins (LDL) (FIG. 15C), a 50% decrease in Triglycerides (FIG. 15D) and a 13% decrease in blood glucose (FIG. 15E) compared with the Control high cholesterol group.

[0027] FIG. 16 shows hamsters treated with compound 1 showed a decrease by 20% in Total Cholesterol compared with the high cholesterol fed group.

[0028] FIG. 17 shows that mice administered with compound 1 showed 66% decreases of TNF-? from the LPS group.

[0029] FIG. 18A shows the body weight of mice administered with compound 1 compared to the control high fat with sucrose group. FIG. 18B shows that mice administered with compound 1 showed a significant (P<0.0001) decrease by 20% in body weight from the control high fat with sucrose group.

[0030] FIG. 19 shows that the group of mice administered with compound 1 showed a significant (P<0.04) decrease by 18% in fasting blood glucose from the control high fat with sucrose group.

[0031] FIG. 20 shows that mice administered with compound 1 showed a significant (P<0.009) decrease by 25% in fasting blood glucose from the control high fat with sucrose group (FIG. 21A). An oral glucose tolerance test was conducted. For this test the mice were administered with glucose orally at 2 g/Kg. Blood glucose was measured at the fasted state (baseline, taken prior to glucose administration), then at 30, 60, 90 and 120 minutes (FIG. 20B). The group of mice treated with compound 1 showed significant (P<0.004) decrease by 28% in blood glucose at the peak time of 30 minutes (FIG. 20C).

[0032] FIG. 21 shows that mice administered with compound 1 showed a 19% decrease in liver weight compared with the high fat with sucrose group.

[0033] FIG. 22 shows that mice administered with compound 1 showed a 22% decrease in abdominal fat weight compared with the high fat with sucrose group.

[0034] FIGS. 23A and B show that Mice treated with compound 5 showed an 11% decrease in body weight compared with the Control high fat diet group.

[0035] FIG. 24A shows that the group of mice administered with compound 5 showed an 8% decrease in fasting blood glucose, compared with the control high fat diet group. FIG. 24B shows the effect of compounds 2, 3, 4, and 5 on oral glucose tolerance test at 60 days. The group of mice treated with compound 5 showed significant (P<0.03) decrease by 32% in blood glucose at the peak time of 30 minutes compared with the control high fat diet group in the oral glucose tolerance test (FIG. 24C).

[0036] FIG. 25A shows the effect of compound 2, 3, 4, and 5 on fasting blood glucose at Day 90.

[0037] FIG. 25B shows the effect of compound 2, 3, 4, and 5 on oral glucose tolerance test at Day 90.

[0038] FIG. 25C shows that mice treated with compound 5 showed a decrease by 19% in blood glucose at the peak time of 30 minutes in the oral glucose tolerance test when compared with the control high fat diet group.

[0039] FIG. 26 shows that mice treated with compound 6 showed 10% reduction in fasting blood glucose on day 60 (FIG. 26A) and an 11% decrease on day 90 (FIG. 26B), compared with the control high fat diet group.

[0040] FIG. 27 shows that mice treated with compound 7 showed 7% reduction in fasting blood glucose on day 60 compared with the control high fat diet group.

[0041] FIG. 28A shows that compound 6 showed a significant (P<0.0001) decrease by 5% in body weight compared with the control group. FIG. 28B shows that at the end of 90 days, the group of mice treated with compound 6 showed a significant (P<0.0001) decrease by 15% in body weight compared with the Control high fat diet group.

[0042] FIG. 29A shows the effect of compound 8 on oral glucose tolerance test at 90 days. FIG. 29B shows that in the oral glucose tolerance test these mice also showed 23% reduction in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the control high fat diet group. FIG. 29C shows that mice treated with compound 8 showed a significant (P<0.02) decrease by 26% in fasting blood glucose compared with the control high fat diet group.

[0043] FIG. 30 shows that rats treated with compound 8 showed 4% decrease in systolic blood pressure and 8% decrease in diastolic blood pressure, then the vehicle group.

[0044] FIG. 31 shows that hamsters treated with compound 8 showed a significant decrease (P<0.05) by 31% in triglycerides compared with the high fructose fed group.

[0045] FIG. 32 shows that mice administered with compound 8 showed a 59% decrease of TNF-? from the LPS group.

[0046] FIG. 33A shows that mice treated with compound 9 showed a significant (P<0.0001) decrease by 5% in body weight when compared to the high fat diet control group. FIG. 33B shows mice treated with compound 9 showed a significant (P<0.0001) decrease by 15% in percent body weight when compared to the high fat diet control group.

[0047] FIG. 34A shows the effect of compound 9 on oral glucose tolerance test at Day 90. FIG. 34B shows that mice treated with compound 9 showed 8% reduction in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the control high fat diet group.

DETAILED DESCRIPTION OF THE INVENTION

[0048] In an embodiment of the present invention, the groups represented as R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 on ring A are predominantly hydrogen.

[0049] In an embodiment of the present invention, the group represented by R.sub.7 is a carbonyl group through which free amino group containing molecules can form condensates. R.sub.7 can also be selected from groups such as ethanedithiol and propanedithiol.

[0050] In an embodiment of the present invention, the styryl ring represented as ring A can contain one or multiple side chain substituents ranging from hydrogen, phenoxy, amino, sulphonyl, substituted, unsubstituted, straight chain or branched alkyls derivatives, halogens, and the like. This also defines the range of substituents accommodated by R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5.

[0051] In an embodiment of the present invention, the groups represented by R.sub.6 and R.sub.8 on ring B can be selected from hydrogen, Hydroxy, alkoxy and branched or unbranched alkyl derivatives.

[0052] In an embodiment of the present invention, the groups represented by X and Y on ring B can be selected from hydrogen or Halogens like fluorine, chlorine, bromine, and iodine.

[0053] Pharmaceutically acceptable salts forming part of this invention include base addition salts such as alkali metal salts like Li, Na, and K salts, alkaline earth metal salts like Ca and Mg salts, salts of organic bases such as lysine, arginine, guanidine, diethanolamine, chlorine and the like, ammonium or substituted ammonium salts. Salts may include acid addition salts which are sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartarates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, ascorbates, glycerophosphates, ketoglutarates and the like. Pharmaceutically acceptable solvates may be hydrates or comprising other solvents of crystallization such as alcohols

[0054] More preferably, the present innovation relates to novel Styryl Carboxylate compounds of formula (I),

##STR00002##

[0055] their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates and pharmaceutical compositions containing them, wherein, the groups represented as R.sub.6 and R.sub.8, in the ring B are selected from hydrogen and alkoxy derivatives. The group represented by R.sub.7 on ring B will be a carbonyl group which forms Schiff bases with compounds having a free amino group and forms thioketalization with compounds like ethanedithiol and propandithiol. The benzene ring represented as Ring A can contain substituents represented by R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 that are selected from linear or branched, substituted or unsubstituted (C.sub.1 to C.sub.12) alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, nonyl and the like; substituted or unsubstituted (C.sub.1-C.sub.12) alkoxy group such as methoxy, ethoxy, propoxy, butoxy and the like; hydroxyl group or extended chain through an alkyloxy ester or un-substituted or substituted aryloxy ester groups; amines, sulphonyl, halogens and the like. The groups represented by X and Y on ring B are preferentially selected from hydrogen and Halogens like fluorine, chlorine, bromine and iodine.

[0056] The formula of the useful compounds synthesized in this present are listed below. [0057] 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-phenyl ester (C1) [0058] 4-((E)-ureidomethyl)phenyl cinnamate (C2) [0059] 4-(1,3-dithian-2-yl)phenyl cinnamate (C3) [0060] 3-Phenyl-acrylic acid 4-benzylidineamino-3-hydroxyaniline-2-methoxy-phenyl ester (C4) [0061] 4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate (C5) [0062] (E)-ethyl 4-(4-(cinnamoyloxy)-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (C6) [0063] (E)-ethyl 4-(4-(cinnamoyloxy)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (C7) [0064] 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl ester (C8) [0065] 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate (C9) [0066] 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (C10) [0067] 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl ester (C11) [0068] 4-formyl-2-methoxyphenyl cinnamate [0069] 2-chloro-4-formyl-6-methoxyphenyl cinnamate [0070] 2-bromo-4-formyl-6-methoxyphenyl cinnamate [0071] 4-formylphenyl cinnamate [0072] (E)-4-formyl-2-methoxyphenyl 3-(3-chlorophenyl)acrylate [0073] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0074] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0075] (E)-4-formylphenyl 3-(3-chlorophenyl)acrylate [0076] (E)-4-formyl-2-methoxyphenyl 3-(3-bromophenyl)acrylate [0077] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0078] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0079] (E)-4-formylphenyl 3-(3-bromophenyl)acrylate [0080] (E)-4-formyl-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0081] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0082] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0083] (E)-4-formylphenyl 3-(3-methoxyphenyl)acrylate [0084] (E)-4-formyl-2-methoxyphenyl 3-(4-chlorophenyl)acrylate [0085] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0086] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0087] (E)-4-formylphenyl 3-(4-chlorophenyl)acrylate [0088] (E)-4-formyl-2-methoxyphenyl 3-(4-bromophenyl)acrylate [0089] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0090] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0091] (E)-4-formylphenyl 3-(4-bromophenyl)acrylate [0092] (E)-4-formyl-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0093] (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0094] (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0095] (E)-4-formylphenyl 3-(4-methoxyphenyl)acrylate [0096] 4-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)benzoic acid [0097] 4-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic acid [0098] 4-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic acid [0099] 4-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)benzoic acid [0100] 4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid [0101] 4-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0102] 4-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0103] 4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic acid [0104] 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid [0105] 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic acid [0106] 4-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0107] 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)benzoic acid [0108] 4-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0109] 4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0110] 4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0111] 4-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0112] 4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid [0113] 4-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0114] 4-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0115] 4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic acid [0116] 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid [0117] 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic acid [0118] 4-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid [0119] 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)benzoic acid [0120] 4-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0121] 4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0122] 4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0123] 4-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid [0124] 2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid [0125] 2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0126] 2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0127] 2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylbutanoic acid [0128] 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid [0129] 2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0130] 2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0131] 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0132] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid [0133] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0134] 2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0135] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0136] 2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0137] 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0138] 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0139] 2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0140] 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid [0141] 2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0142] 2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0143] 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0144] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid [0145] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0146] 2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid [0147] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0148] 2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0149] 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0150] 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0151] 2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid [0152] 2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid [0153] 2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0154] 2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0155] 2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylpentanoic acid [0156] 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid [0157] 2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0158] 2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0159] 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0160] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid [0161] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0162] 2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0163] 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0164] 2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0165] 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0166] 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0167] 2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0168] 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid [0169] 2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0170] 2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0171] 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0172] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid [0173] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0174] 2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid [0175] 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0176] 2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0177] 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0178] 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0179] 2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid [0180] 4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate [0181] 2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate [0182] 2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate [0183] 4-((E)-(hydroxyimino)methyl)phenyl cinnamate [0184] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate [0185] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0186] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0187] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-chlorophenyl)acrylate [0188] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate [0189] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0190] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0191] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-bromophenyl)acrylate [0192] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0193] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0194] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0195] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-methoxyphenyl)acrylate [0196] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate [0197] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0198] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0199] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-chlorophenyl)acrylate [0200] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate [0201] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0202] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0203] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-bromophenyl)acrylate [0204] (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0205] (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0206] (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0207] (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-methoxyphenyl)acrylate [0208] 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate [0209] 2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate [0210] 2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate [0211] 4-((E)-ureidomethyl)phenyl cinnamate [0212] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate [0213] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate [0214] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate [0215] (E)-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate [0216] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate [0217] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate [0218] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate [0219] (E)-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate [0220] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate [0221] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate [0222] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate [0223] (E)-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate [0224] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate [0225] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate [0226] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate [0227] (E)-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate [0228] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate [0229] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate [0230] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate [0231] (E)-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate [0232] (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate [0233] (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate [0234] (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate [0235] (E)-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate [0236] 4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl cinnamate [0237] 2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl cinnamate [0238] 2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl cinnamate [0239] 4-((E)-(4-hydroxyphenylimino)methyl)phenyl cinnamate [0240] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate [0241] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0242] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0243] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-chlorophenyl)acrylate [0244] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate [0245] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0246] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0247] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-bromophenyl)acrylate [0248] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0249] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0250] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0251] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-methoxyphenyl)acrylate [0252] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate [0253] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0254] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0255] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-chlorophenyl)acrylate [0256] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate [0257] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0258] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0259] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-bromophenyl)acrylate [0260] (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0261] (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0262] (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0263] (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-methoxyphenyl)acrylate [0264] 4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl cinnamate [0265] 2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl cinnamate [0266] 2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl cinnamate [0267] 4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl cinnamate [0268] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate [0269] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0270] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate [0271] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(3-chlorophenyl)acrylate [0272] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate [0273] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0274] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate [0275] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(3-bromophenyl)acrylate [0276] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0277] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0278] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate [0279] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(3-methoxyphenyl)acrylate [0280] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate [0281] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0282] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate [0283] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(4-chlorophenyl)acrylate [0284] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate [0285] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0286] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate [0287] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(4-bromophenyl)acrylate [0288] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0289] (E)-2-chloro-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0290] (E)-2-bromo-4-((E)-(2-4-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate [0291] (E)-4-((E)-(2-4-dinitrophenylhydrazo)methyl)phenyl 3-(4-methoxyphenyl)acrylate

[0292] The list also consists of the IUPAC names of the compounds given the table below

TABLE-US-00001 (4a) [00003] S.No R7 R8 R6 R2 R3 1. O OCH.sub.3 H H H 2. O OCH.sub.3 Cl H H 3. O OCH.sub.3 Br H H 4. O H H H H 5. O OCH.sub.3 H Cl H 6. O OCH.sub.3 Cl Cl H 7. O OCH.sub.3 Br Cl H 8. O H H Cl H 9. O OCH.sub.3 H Br H 10. O OCH.sub.3 Cl Br H 11. O OCH.sub.3 Br Br H 12. O H H Br H 13. O OCH.sub.3 H OCH.sub.3 H 14. O OCH.sub.3 Cl OCH.sub.3 H 15. O OCH.sub.3 Br OCH.sub.3 H 16. O H H OCH.sub.3 H 17. O OCH.sub.3 H H Cl 18. O OCH.sub.3 Cl H Cl 19. O OCH.sub.3 Br H Cl 20. O H H H Cl 21. O OCH.sub.3 H H Br 22. O OCH.sub.3 Cl H Br 23. O OCH.sub.3 Br H Br 24. O H H H Br 25. O OCH.sub.3 H H OCH.sub.3 26. O OCH.sub.3 Cl H OCH.sub.3 27. O OCH.sub.3 Br H OCH.sub.3 28. O H H H OCH.sub.3 29. [00004] OCH.sub.3 H H H 30. [00005] OCH.sub.3 Cl H H 31. [00006] OCH.sub.3 Br H H 32. [00007] H H H H 33. [00008] OCH.sub.3 H Cl H 34. [00009] OCH.sub.3 Cl Cl H 35. [00010] OCH.sub.3 Br Cl H 36. [00011] H H Cl H 37. [00012] OCH.sub.3 H Br H 38. [00013] OCH.sub.3 Cl Br H 39. [00014] OCH.sub.3 Br Br H 40. [00015] H H Br H 41. [00016] OCH.sub.3 H OCH.sub.3 H 42. [00017] OCH.sub.3 Cl OCH.sub.3 H 43. [00018] OCH.sub.3 Br OCH.sub.3 H 44. [00019] H H OCH.sub.3 H 45. [00020] OCH.sub.3 H H Cl 46. [00021] OCH.sub.3 Cl H Cl 47. [00022] OCH.sub.3 Br H Cl 48. [00023] H H H Cl 49. [00024] OCH.sub.3 H H Br 50. [00025] OCH.sub.3 Cl H Br 51. [00026] OCH.sub.3 Br H Br 52. [00027] H H H Br 53. [00028] OCH.sub.3 H H OCH.sub.3 54. [00029] OCH.sub.3 Cl H OCH.sub.3 55. [00030] OCH.sub.3 Br H OCH.sub.3 56. [00031] H H H OCH.sub.3 57. [00032] OCH.sub.3 H H H 58. [00033] OCH.sub.3 Cl H H 59. [00034] OCH.sub.3 Br H H 60. [00035] H H H H 61. [00036] OCH.sub.3 H Cl H 62. [00037] OCH.sub.3 Cl Cl H 63. [00038] OCH.sub.3 Br Cl H 64. [00039] H H Cl H 65. [00040] OCH.sub.3 H Br H 66. [00041] OCH.sub.3 Cl Br H 67. [00042] OCH.sub.3 Br Br H 68. [00043] H H Br H 69. [00044] OCH.sub.3 H OCH.sub.3 H 70. [00045] OCH.sub.3 Cl OCH.sub.3 H 71. [00046] OCH.sub.3 Br OCH.sub.3 H 72. [00047] H H OCH.sub.3 H 73. [00048] OCH.sub.3 H H Cl 74. [00049] OCH.sub.3 Cl H Cl 75. [00050] OCH.sub.3 Br H Cl 76. [00051] H H H Cl 77. [00052] OCH.sub.3 H H Br 78. [00053] OCH.sub.3 Cl H Br 79. [00054] OCH.sub.3 Br H Br 80. [00055] H H H Br 81. [00056] OCH.sub.3 H H OCH.sub.3 82. [00057] OCH.sub.3 Cl H OCH.sub.3 83. [00058] OCH.sub.3 Br H OCH.sub.3 84. [00059] H H H OCH.sub.3 85. [00060] OCH.sub.3 H H H 86. [00061] OCH.sub.3 Cl H H 87. [00062] OCH.sub.3 Br H H 88. [00063] H H H H 89. [00064] OCH.sub.3 H Cl H 90. [00065] OCH.sub.3 Cl Cl H 91. [00066] OCH.sub.3 Br Cl H 92. [00067] H H Cl H 93. [00068] OCH.sub.3 H Br H 94. [00069] OCH.sub.3 Cl Br H 95. [00070] OCH.sub.3 Br Br H 96. [00071] H H Br H 97. [00072] OCH.sub.3 H OCH.sub.3 H 98. [00073] OCH.sub.3 Cl OCH.sub.3 H 99. [00074] OCH.sub.3 Br OCH.sub.3 H 100. [00075] H H OCH.sub.3 H 101. [00076] OCH.sub.3 H H Cl 102. [00077] OCH.sub.3 Cl H Cl 103. [00078] OCH.sub.3 Br H Cl 104. [00079] H H H Cl 105. [00080] OCH.sub.3 H H Br 106. [00081] OCH.sub.3 Cl H Br 107. [00082] OCH.sub.3 Br H Br 108. [00083] H H H Br 109. [00084] OCH.sub.3 H H OCH.sub.3 110. [00085] OCH.sub.3 Cl H OCH.sub.3 111. [00086] OCH.sub.3 Br H OCH.sub.3 112. [00087] H H H OCH.sub.3 113. NOH OCH.sub.3 H H H 114. NOH OCH.sub.3 Cl H H 115. NOH OCH.sub.3 Br H H 116. NOH H H H H 117. NOH OCH.sub.3 H Cl H 118. NOH OCH.sub.3 Cl Cl H 119. NOH OCH.sub.3 Br Cl H 120. NOH H H Cl H 121. NOH OCH.sub.3 H Br H 122. NOH OCH.sub.3 Cl Br H 123. NOH OCH.sub.3 Br Br H 124. NOH H H Br H 125. NOH OCH.sub.3 H OCH.sub.3 H 126. NOH OCH.sub.3 Cl OCH.sub.3 H 127. NOH OCH.sub.3 Br OCH.sub.3 H 128. NOH H H OCH.sub.3 H 129. NOH OCH.sub.3 H H Cl 130. NOH OCH.sub.3 Cl H Cl 131. NOH OCH.sub.3 Br H Cl 132. NOH H H H Cl 133. NOH OCH.sub.3 H H Br 134. NOH OCH.sub.3 Cl H Br 135. NOH OCH.sub.3 Br H Br 136. NOH H H H Br 137. NOH OCH.sub.3 H H OCH.sub.3 138. NOH OCH.sub.3 Cl H OCH.sub.3 139. NOH OCH.sub.3 Br H OCH.sub.3 140. NOH H H H OCH.sub.3 141. NCONH.sub.2 OCH.sub.3 H H H 142. NCONH.sub.2 OCH.sub.3 Cl H H 143. NCONH.sub.2 OCH.sub.3 Br H H 144. NCONH.sub.2 H H H H 145. NCONH.sub.2 OCH.sub.3 H Cl H 146. NCONH.sub.2 OCH.sub.3 Cl Cl H 147. NCONH.sub.2 OCH.sub.3 Br Cl H 148. NCONH.sub.2 H H Cl H 149. NCONH.sub.2 OCH.sub.3 H Br H 150. NCONH.sub.2 OCH.sub.3 Cl Br H 151. NCONH.sub.2 OCH.sub.3 Br Br H 152. NCONH.sub.2 H H Br H 153. NCONH.sub.2 OCH.sub.3 H OCH.sub.3 H 154. NCONH.sub.2 OCH.sub.3 Cl OCH.sub.3 H 155. NCONH.sub.2 OCH.sub.3 Br OCH.sub.3 H 156. NCONH.sub.2 H H OCH.sub.3 H 157. NCONH.sub.2 OCH.sub.3 H H Cl 158. NCONH.sub.2 OCH.sub.3 Cl H Cl 159. NCONH.sub.2 OCH.sub.3 Br H Cl 160. NCONH.sub.2 H H H Cl 161. NCONH.sub.2 OCH.sub.3 H H Br 162. NCONH.sub.2 OCH.sub.3 Cl H Br 163. NCONH.sub.2 OCH.sub.3 Br H Br 164. NCONH.sub.2 H H H Br 165. NCONH.sub.2 OCH.sub.3 H H OCH.sub.3 166. NCONH.sub.2 OCH.sub.3 Cl H OCH.sub.3 167. NCONH.sub.2 OCH.sub.3 Br H OCH.sub.3 168. NCONH.sub.2 H H H OCH.sub.3 169. [00088] OCH.sub.3 H H H 170. [00089] OCH.sub.3 Cl H H 171. [00090] OCH.sub.3 Br H H 172. [00091] H H H H 173. [00092] OCH.sub.3 H Cl H 174. [00093] OCH.sub.3 Cl Cl H 175. [00094] OCH.sub.3 Br Cl H 176. [00095] H H Cl H 177. [00096] OCH.sub.3 H Br H 178. [00097] OCH.sub.3 Cl Br H 179. [00098] OCH.sub.3 Br Br H 180. [00099] H H Br H 181. [00100] OCH.sub.3 H OCH.sub.3 H 182. [00101] OCH.sub.3 Cl OCH.sub.3 H 183. [00102] OCH.sub.3 Br OCH.sub.3 H 184. [00103] H H OCH.sub.3 H 185. [00104] OCH.sub.3 H H Cl 186. [00105] OCH.sub.3 Cl H Cl 187. [00106] OCH.sub.3 Br H Cl 188. [00107] H H H Cl 189. [00108] OCH.sub.3 H H Br 190. [00109] OCH.sub.3 Cl H Br 191. [00110] OCH.sub.3 Br H Br 192. [00111] H H H Br 193. [00112] OCH.sub.3 H H OCH.sub.3 194. [00113] OCH.sub.3 Cl H OCH.sub.3 195. [00114] OCH.sub.3 Br H OCH.sub.3 196. [00115] H H H OCH.sub.3 197. [00116] OCH.sub.3 H H H 198. [00117] OCH.sub.3 Cl H H 199. [00118] OCH.sub.3 Br H H 200. [00119] H H H H 201. [00120] OCH.sub.3 H Cl H 202. [00121] OCH.sub.3 Cl Cl H 203. [00122] OCH.sub.3 Br Cl H 204. [00123] H H Cl H 205. [00124] OCH.sub.3 H Br H 206. [00125] OCH.sub.3 Cl Br H 207. [00126] OCH.sub.3 Br Br H 208. [00127] H H Br H 209. [00128] OCH.sub.3 H OCH.sub.3 H 210. [00129] OCH.sub.3 Cl OCH.sub.3 H 211. [00130] OCH.sub.3 Br OCH.sub.3 H 212. [00131] H H OCH.sub.3 H 213. [00132] OCH.sub.3 H H Cl 214. [00133] OCH.sub.3 Cl H Cl 215. [00134] OCH.sub.3 Br H Cl 216. [00135] H H H Cl 217. [00136] OCH.sub.3 H H Br 218. [00137] OCH.sub.3 Cl H Br 219. [00138] OCH.sub.3 Br H Br 220. [00139] H H H Br 221. [00140] OCH.sub.3 H H OCH.sub.3 222. [00141] OCH.sub.3 Cl H OCH.sub.3 223. [00142] OCH.sub.3 Br H OCH.sub.3 224. [00143] H H H OCH.sub.3 X = Y hydrogen; R1 = R4 = R5 = hydrogen

[0293] Preferred salts for the compounds listed above are hydrochloride, hydrobromide, sodium, potassium or magnesium.

[0294] According to another feature of this present invention, there is provided a process for the preparation of the compound represented by the formula I, wherein all symbols are as defined as earlier, as shown in scheme(I):

##STR00144##

Structure (4a) is the equivalent structure of (4) where R.sub.7 is as described earlier. In cases where R.sub.7?O, the reaction is only until the second step.

[0295] The reaction of compound of general formula (1a) with thionyl chloride, where the groups R1, R2, R3, R4 and R5 of the compound (1a) have been defined earlier, to produce a compound of the general formula (1b) may be carried out in an inert atmosphere which may be maintained by using inert gases such as Nitrogen, Argon or Helium. Thionyl chloride is added drop wise to the compound (1a) which may be taken as such without any solvents. After addition of thionyl chloride, the reaction mixture is subjected to reflux. The reaction temperature may vary between 20? C. to 150? C., but more preferably between 60? C. to 90? C. The duration of the reaction may range from 1 to 24 hours, preferably between 4 to 6 hours. After refluxing the excess thionyl chloride is distilled off to obtain (1b).

[0296] The reaction of compound of general formula (1b) with a compound of general formula (2a) where the groups R.sub.6, R.sub.7, X and Y have been defined earlier may be carried out using a polar protic solvent like chloroform and in the presence of weak bases like DEA, TEA, Isopropylamine, pyridine, pipridine and the like, but more preferably with a base like TEA. The reaction temperature may range between 0 to 20? C., more preferably in the range of 5-10? C. The reaction time may range from 1 to 10 hours and following completion of the reaction, the product may be extracted from the reaction mixture by washing the organic phase with an aqueous solvent followed by precipitation using non polar solvents like butane, pentante, hexane, cyclohexane etc. to obtain compound of formula (3a).

[0297] The reaction of compound of general formula (3a) with an aliphatic or aromatic amines or amino acids, wherein the amino group reacts, is possible only when R.sub.7 is a keto functional group like (CHO) or (C?O). This reaction may take place in the presence of any alcohol along with catalytic amounts of mineral acids such as sulphuric acid. The reaction temperature may vary from 0 to 100? C. preferably in the range of 50-70? C. and the reaction time may vary between 1 to 24 hours, preferably in the range of 4-7 hours. The schiff base or the imine thus formed may be precipitated or could be extracted after suitable workup procedures such as water quenching. The resultant molecule is the styryl carboxylate of general formula (4a) where the groups have been defined earlier.

[0298] The invention is explained in detail in the examples given below which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.

Example 1

Synthesis of 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-phenyl ester (C1)

[0299] ##STR00145##

Step (i)

Synthesis of Cinnamoyl Chloride

[0300] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-phenyl ester

[0301] 4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii)

Synthesis of 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-phenyl ester

[0302] Stage (ii) compound (2.5 g) was taken in a clean and dry round bottom flask and Methanol (25 ml) was added. The reaction mixture was cooled to 15 C and sodium acetate (2.5 g) was added. Hydroxylamine hydrochloride (1.25 g) dissolved in 10 ml of water was added drop wise to the reaction mixture with constant stirring. Stirring was continued for 4 hours at room temperature. The reaction mixture was then transferred to a beaker containing 100 ml of water. The precipitated solid was filtered, washed with water and then followed by hexane and dried. (Yield 1.2 g)

[0303] The synthesized compound was confirmed by proton NMR.

[0304] 7.25 (d, 1H), 7.61 (d, 1H), 6.67 (d, 1H), 6.64 (d, 1H), 8.17 (s, 1H), 1.28 (s, 1H), 6.674 (d, J=16.5, 1H), 7.929 (d, J=16.5, 1H), 7.28 (d, 1H), 7.24 (t, 1H), 7.23 (t, 1H), 7.46 (t, 1H), 7.45 (d, 1H)

Example 2

Synthesis of 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl ester (C8)

[0305] ##STR00146##

Step (i)

Synthesis of Cinnamoyl Chloride

[0306] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-2-methoxy-phenyl ester (Cinnamoyl vanillin)

[0307] Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10? C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii)

Synthesis of 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl ester

[0308] Cinnamoyl vanniline (5.7 g) was taken in a round bottom flask and methanol (50 ml) was added. The reaction mixture was cooled to 15? C. and sodium acetate (7.89 g) was added. Hydroxyl amine (2.8 g) was dissolved in (25 ml) of water and this was added drop wise to the reaction mixture under constant stirring. The reaction mixture was allowed to stir for 4 hours and then transferred into a beaker containing 100 ml of water. The precipitated solid was filtered, washed with water, followed by hexane and then dried. (Yield 2.8 g)

[0309] 7.25 (d, 1H), 7.61 (d, 1H), 6.67 (d, 1H), 3.85 (s, 3H), 8.17 (s, 1H), 1.28 (s, 1H), 6.674 (d, J=16.5, 1H), 7.929 (d, J=16.5, 1H), 7.28 (d, 1H), 7.24 (t, 1H), 7.23 (t, 1H), 7.46 (t, 1H), 7.45 (d, 1H)

Example 3

Synthesis of 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (C10)

[0310] ##STR00147##

Step (i)

Synthesis of Cinnamoyl Chloride

[0311] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle and stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-2-methoxy-phenyl ester (Cinnamoyl vanillin)

[0312] Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10? C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii)

Synthesis of 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester

[0313] Cinnamoyl vanilline (3.0 g), Urea (0.64 g) and Ethylacetoacetate (2.56 ml) were taken in a clean and dry three neck round bottom flask and Methanol (50 ml) and Sulphuric acid (5 drops) were added. This reaction mixture was subjected to reflux at 60-80? C. for 5 hours. After reflux, the reaction mixture was transferred to a beaker containing 200 ml of water. The precipitated solid was filtered, washed with water and followed with hexane and then dried. (Yield 1.42 g)

[0314] 5.61 (s, 1H), 5.53 (s, 1H), 6.51 (s, 1H), 6.83 (d, 2H), 4.21 (m, 2H), 1.26 (t, 3H), 2.23 (s, 3H), 3.91 (s, 3H), 6.8 (d, 1H, J=16.5), 7.9 (d, 1H, J=16.5), 7.40 (d, 2H), 7.25 (t, 1H,)

Example 4

Synthesis of 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate (C9)

[0315] ##STR00148##

Synthesis of Cinnamoyl Chloride

Step (i)

[0316] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-2-methoxy-phenyl ester (Cinnamoyl vanillin)

[0317] Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10? C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii)

Synthesis of 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate

[0318] Cinnamoyl vanillin (5.0 g) was taken in a two next round bottom flask along with urea (2.2 g). Toulene (25 ml) was added and stirred and catalytic amounts of Paratoulylsulphonic acid (0.1 g) was added. The reaction mixture was refluxed for 4 hours at 100-110? C. After reflux the solvent was removed by distillation and the product was washed with water and followed by hexane and then dried. (Yield 3.12 g)

NMR Assignment

[0319] 7.10 (1H, d), 7.20 (1H, d), 7.10 (1H, s), 3.80 (3H, s), 8.15 (1H, s), 6.20(1H,d,J=16.5 MHz), 7.71(1H,d,J=16.5 MHz), 7.35(1H,d,Aromatic)

Example 5

[0320] ##STR00149##

Synthesis of 3-Phenyl-acrylic acid 4-benzylidineamino-3-hydroxyaniline-2-methoxy-phenyl ester (C4)

Step (i)

Synthesis of Cinnamoyl Chloride

[0321] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-2-methoxy-phenyl ester (Cinnamoyl vanillin)

[0322] Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10? C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

[0323] Cinnamoyl vanillin (1.5 g) was taken in a clean two neck round bottom flask and Ethanol (25 ml) was added with stirring. 3-Aminophenol (0.6 g) was added lot by lot with constant stirring. After completion of addition, 2 drops of sulphuric acid was added. The reaction mixture was refluxed for 4 hours at 75-80? C. The solid product formed was filtered and washed with Ethanol and followed by water and finally by hexane and dried. (Yield 0.89 g)

NMR Assignment

[0324] 6.81 (1H, d), 7.15 (1H, d), 7.10 (1H, s), 3.91 (3H, s), 6.72 to 7.10(Aromatic), 6.20(1H,d,J=16.5 MHz), 7.71(1H,d,J=16.5 MHz), 7.15 to 7.35(Aromatic)

Example 6

[0325] ##STR00150##

Synthesis of 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl ester (C11)

Step (i)

Synthesis of Cinnamoyl Chloride

[0326] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-phenyl ester

[0327] 4-hydroxy benzaldehyde (14.69 g) was taken is a clean and dry two neck round bottom flask and Chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10? C. Nicotinyl chloride (20.0 g) was added drop wise and stirring was continued for 15 minutes. TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii)

Synthesis of 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl ester

[0328] Cinnamoyl 4-hydroxy benzaldehyde (1 g) was taken in a clean and dry round bottom flask and methanol (10 ml) was added. 2,4 Dinitrophenylhydrazine (0.00 g) was added slowly into the reaction mixture and methanol (20 ml) was added. The reaction mixture was allowed to stir for 3 hours at room temperature. The solid formed was then filtered and washed with water and followed by hexane. (Yield 0.85 g)

NMR Assignment

[0329] 6.81 (1H, d), 7.15 (1H, d), 7.6(1H,s), 7.12 (1H, d), 8.30 (1H, s), 5.0(1H,s), 8.5(1H,s), 8.21 (1H, d), 6.62 (1H, d), 6.20(1H,d,J=16.5 MHz), 7.71(1H,d,J=16.5 MHz), 7.15 to 7.35(Aromatic)

Example 7

[0330] ##STR00151##

Synthesis of 4-((E)-ureidomethyl)phenyl cinnamate (C2)

Step (i)

Synthesis of Cinnamoyl Chloride

[0331] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-phenyl ester

[0332] 4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii)

Synthesis of 4-((E)-ureidomethyl)phenyl cinnamate

[0333] Compound of step 2 (5 g) was taken in a clean and dry two neck round bottom flask and PTSA (3.8 g) was added. Urea (1.3 g) was then added and Toulene (50 ml) was added with stirring. The reaction mixture was refluxed for 5 hours at 100-110 and allowed to cool over night at room temperature. The precipitated compound was filtered, washed with water and followed by hexane and dried. (Yield 3.34 g)

NMR Assignment

[0334] 7.10 to 7.60 (Aromatic), 8.20 (1H, s), 5.0(2H,s), 6.20(1H,d,J=16.5 MHz), 7.71(1H,d,J=16.5 MHz), 7.15 to 7.35(Aromatic)

Example 8

[0335] ##STR00152##

Synthesis of 4-(1,3-dithian-2-yl)phenyl cinnamate (C3)

Step (i)

Synthesis of Cinnamoyl Chloride

[0336] Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80? C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii)

Synthesis of 3-Phenyl-acrylic acid 4-formyl-phenyl ester

[0337] 4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2?250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2?250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii)

Synthesis of 4-(1,3-dithian-2-yl)phenyl cinnamate

[0338] Compound from step (ii) (6.0 g) was taken in a clean and dry two nek round bottom flask and Chloroform (60 ml) was added with stirring. 1,3 Dithiane (2.7 g) and catalytic amount of iodine (0.1 g) was added and the reaction mixture was allowed to stir at room temperature for 5 hours. It was then quenched with cold water and the organic layer was separated which was further washed with water. The chloroform layer was then concentrated and the solid obtained was filtered, washed with hexane and then dried. (Yield 7.0 g)

NMR Assignment

[0339] 2.44 (4H, t,), 2.03 (2H, m), 4.5 (2H, s), 6.8-7.1(Aromatic), 6.20(1H,d,J=16.5 MHz), 7.71(1H,d,J=16.5 MHz), 7.15-7.35 (Aromatic)