Androgenic and Anti-Androgenic Effects of Progesterone Derivatives with Different Halogens as Substituents at the C-6 Position

The 1999 study explored the impact of halogen substitution on the androgenic and anti-androgenic activities of progesterone derivatives. Four compounds were synthesized and tested on castrated male hamster flank organs and seminal vesicles. Compounds 7 and 8 were inactive, while compound 10, with a bromine atom, showed anti-androgenic effects by inhibiting the conversion of testosterone to dihydrotestosterone (DHT). Compound 11, with a chlorine atom, exhibited androgenic effects at low doses but anti-androgenic effects at high doses by inhibiting DHT formation. The study concluded that the electronegativity of the halogen at the C-6 position is critical in determining the biological activity of these steroids, with potential implications for treating androgen-dependent diseases. Compound 10 inhibited T to DHT conversion, while compound 11 had a dose-dependent effect on this conversion and protein synthesis in seminal vesicles, suggesting the importance of halogen electronegativity in these processes.