Synthesis of novel estradiol Thiosemicarbazone derivatives as potential antiestrogens

A simple, efficient and selective method for the preparation of 2-formylestradiol was described. The methodology involved the use of a modified Sommelet reaction and provided a good yield of pure product, which was characterized by spectroscopy. Then, conversion of the aldehydic group into various thiosemicarbazone moieties was undertaken. Out of the thiosemicarbazone derivatives, the phenylthiosemicarbazone VI exhibited 85% uterotrophic activity relative to estradiol, while the other members of the series showed a weak uterotrophic activity [39-54%] based on dry uterine weight gain. None of the synthesized compounds elicited anti-fertility activity as assessed by the postcoital anti-implantation activity test