The present disclosure relates to HIF-2 inhibitors and methods of making and using them for treating cancer. Certain compounds were potent in HIF-2 scintillation proximity assay, luciferase assay, and VEGF ELISA assay, and led to tumor size reduction and regression in 786-O xenograft bearing mice in vivo.

The present invention relates to an anthracene derivative compound having a characteristic structure in which an aliphatic aromatic mixed ring group is substituted, and to an organic light-emitting device comprising same. The present invention relates to a high-efficiency and long-lifespan organic light-emitting device having remarkably improved luminous efficiency and lifespan characteristics by adopting the anthracene derivative compound according to the present invention as a host of a light-emitting layer, and adopting a polycyclic compound having a characteristic structure as a dopant of the light-emitting layer.

The present invention relates to an anthracene derivative compound having a characteristic structure in which an aliphatic aromatic mixed ring group is substituted, and to an organic light-emitting device comprising same. The present invention relates to a high-efficiency and long-lifespan organic light-emitting device having remarkably improved luminous efficiency and lifespan characteristics by adopting the anthracene derivative compound according to the present invention as a host of a light-emitting layer, and adopting a polycyclic compound having a characteristic structure as a dopant of the light-emitting layer.

A method of forming a composition comprising contacting a fuel and at least one compound of Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than 70 eV produces at least one ion having a mass-to-charge ratio of 300 to 600.

A method of forming a composition comprising contacting a fuel and at least one compound of Formula I: ##STR00001##
wherein X is carbon, oxygen, or sulfur; R.sup.1 and R.sup.2 each independently are hydrogen, a C.sub.1 to C.sub.20 alkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.3 and R.sup.3 each independently are hydrogen or a C.sub.1 to C.sub.4 alkyl; R.sup.4 and R.sup.4 each independently are hydrogen, a C.sub.1 to C.sub.4 alkyl, a C.sub.4 to C.sub.10 cycloalkyl, or a C.sub.6 to C.sub.10 aryl; R.sup.5 and R.sup.5 each independently are a C.sub.4 to C.sub.10 alkyl; R.sup.6 and R.sup.6 each independently are hydrogen or a C.sub.1 to C.sub.6 alkyl; and R.sup.7 and R.sup.7 each independently are hydrogen or C.sub.1 to C.sub.4 alkyl; and wherein the compound of Formula I when subjected to GC-MS using electron ionization at greater than 70 eV produces at least one ion having a mass-to-charge ratio of 300 to 600.

A compound of the formula (2) ##STR00001##
wherein R.sup.3 and R.sup.4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R.sup.3 and R.sup.4 are quaternary, m and n are each a real number of at least zero, and 2.0m+n3.0.

A compound of the formula (2) ##STR00001##
wherein R.sup.3 and R.sup.4 are the same or different and are a branched hydrocarbon group having 10 to 26 carbon atoms, 42 to 100 mole % of the benzylic carbons of each R.sup.3 and R.sup.4 are quaternary, m and n are each a real number of at least zero, and 2.0m+n3.0.

A calix[4]arenes of the formula (1a),

##STR00001##

wherein: Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are selected from hydrogen, halogen, NO.sub.2, N.sub.3, CN, CHO, COOR, CONR.sub.2, NR.sub.2, triazole moiety and C.sub.1-C.sub.3-alkyl group, the C.sub.1-C.sub.3-alkyl group being optionally substituted, Z is a heterocyclic moiety which is selected from the group including of imidazole, benzimidazole, benzothiazole, benzoxazole, purine, tetrazine, oxazole, pyrazole and thiazole, the heterocyclic moiety being optionally substituted, R.sub.1 and R.sub.2 are selected from hydrogen and C.sub.1-C.sub.8-alkyl, the C.sub.1-C.sub.8-alkyl group being optionally substituted, n being an integer between 1 and 4, They exhibit high cytotoxicity against cancer cells.

A calix[4]arenes of the formula (1a),

##STR00001##

wherein: Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are selected from hydrogen, halogen, NO.sub.2, N.sub.3, CN, CHO, COOR, CONR.sub.2, NR.sub.2, triazole moiety and C.sub.1-C.sub.3-alkyl group, the C.sub.1-C.sub.3-alkyl group being optionally substituted, Z is a heterocyclic moiety which is selected from the group including of imidazole, benzimidazole, benzothiazole, benzoxazole, purine, tetrazine, oxazole, pyrazole and thiazole, the heterocyclic moiety being optionally substituted, R.sub.1 and R.sub.2 are selected from hydrogen and C.sub.1-C.sub.8-alkyl, the C.sub.1-C.sub.8-alkyl group being optionally substituted, n being an integer between 1 and 4, They exhibit high cytotoxicity against cancer cells.

One aspect of the present invention relates to a dinaphthyl ether compound represented by formula (1): ##STR00001##
in the formula (1), R.sup.1 and R.sup.2 are the same or different and each represent a linear or branched hydrocarbon group having 6 to 32 carbon atoms; m and n are each a real number of 0 or more and satisfy 1.0m+n3.0.