Synthesis of alpha-methyl-benzamido-alpha'-substituted styryl cyclohexanone thiosemicarbazones as potential antifertility agents.
Cyclohexanone was condensed with N-hydroxymethyl benzamide in conc. sulphuric acid to give alpha-methyl-benzamido-cyclohexanone (I). The reaction of (I) with thiosemicarbazide in ethanol resulted in alpha-methyl-benzamido-cyclohexanone thiosemicarbazone (II). Condensation of (II) with various aromatic aldehydes in the presence of ethanol afforded alpha-methyl-benzamido-alpha'-substituted-styryl-cyclohexanone thiosemicarbazones (III) in yields ranging from 40 to 50 percent. The compounds exhibited pronounced antiimplantation activity in female albino rats.
D000818:Animals; D001549:Benzamides / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D003281:Contraceptives, Postcoital / Q000138:chemical synthesis*; D003283:Contraceptives, Postcoital, Synthetic / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D003512:Cyclohexanones / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology; D004343:Drug Implants; D005260:Female; D051381:Rats; D013343:Styrenes / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology; D013882:Thiosemicarbazones / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology
D001549:Benzamides; D003281:Contraceptives, Postcoital; D003283:Contraceptives, Postcoital, Synthetic; D003510:Cyclohexanes; D003512:Cyclohexanones; D004343:Drug Implants; D013343:Styrenes; D013882:Thiosemicarbazones