The present disclosure is directed to novel derivatives of naturally occurring humulones and lupulones, methods of making them, compositions comprising them, and methods for using them.

The present disclosure is directed to novel derivatives of naturally occurring humulones and lupulones, methods of making them, compositions comprising them, and methods for using them.

The present disclosure provides compounds and methods for inhibiting or degrading the N-terminal domain of the androgen receptor, as well as methods for treating cancers such as prostate cancer.

The present disclosure provides compounds and methods for inhibiting or degrading the N-terminal domain of the androgen receptor, as well as methods for treating cancers such as prostate cancer.

Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.

Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.

The disclosure relates to an entecavir intermediate, a synthetic method therefor, and the synthetic method for entecavir by using the intermediate. According to the disclosure, the synthetic methods for entecavir and the intermediate thereof have the advantages of being controllable in chirality, high in yield and product purity, wide in source of raw materials, cheap and available in reagents, simple in reactions, convenient to operate, environmentally friendly, and suitable for industrial amplification production.

The disclosure relates to an entecavir intermediate, a synthetic method therefor, and the synthetic method for entecavir by using the intermediate. According to the disclosure, the synthetic methods for entecavir and the intermediate thereof have the advantages of being controllable in chirality, high in yield and product purity, wide in source of raw materials, cheap and available in reagents, simple in reactions, convenient to operate, environmentally friendly, and suitable for industrial amplification production.

[Problem] The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like. [Solution] According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.

[Problem] The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like. [Solution] According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.