Synthesis and Antiandrogenic Activity of 16β-Substituted-17β-hydroxysteroids

Abstract

In order to examine the antiandrogenic activity, a series of 16β-substituted-17β-hydroxysteroids (9 and 16) were synthesized by stereoselective introduction of β-substituents at position 16 of steroids. The corresponding 6-chloro-16β-substituted-17β-hydroxysteroids (20 and 28) and 1, 2α-methylene derivative (36) were also prepared. Among these new steroids synthesized, 17β-hydroxy-16β-ethylestr-4-en-3-one (9b : TSAA-291) was found to have the most potent antiandrogenic activity with very weak side effects and also found to be useful for a treatment of the benign prostatic hypertrophy.