Synthesis, uterotrophic, and antiuterotrophic activities of some estradiol derivatives containing thiadiazole, thiazoline, and thiazolidinone moieties

Article abstract of DOI:10.1002/ardp.19973300906

The effect of structural modification on the biological activity of hormones has been studied on five novel series of estradiol analogs bearing a variety of substituents at the 2-position of the steroidal nucleus. The synthesized compounds include 2-[2-(5-substituted amino-1,3-thiadiazol-2-yl)vinyl]estradiol 17β-acetate 5-9, 2-aroylmethylestradiols 10-12, 2-[2-aryl-2-(substituted thiocarbamoylhydrazono)ethyl)estradiols 13-18 and their cyclic thiazoline 19-24, and thiazolidinone derivatives 25-30. Among the products, the p-hydroxybenzoylmethylestradiol 12 exhibited the highest antiestrogenic activity of 63%. It also elicited 34% of the uterotrophic activity of estradiol.