Synthesis Of 4-Aza-17-Amino Steroidal Acylamides And Studies On Their Inhibition Of 5α-Reductase

Androstenedione(AD), as a new steroid material, attracts chemists'attention because of the shortage of diosgenin resource and the successful synthesis by degradation of sterols. The synthesis of steroids and its intermediates from AD has been the hotspot of steroid industry nowadays.15 acylamino compounds from AD were synthesized by cleavage of A-ring through NaIO4/KMnO4 oxidation, ring closure by amination, oximation with hydroxylaminechloride in C-17 position, and reduction of oxime in C-17 position and substitution with substituted acylchloride and carboxylic acids. The structures of all intermediates and compounds were identified by MS, 1H NMR and 13C NMR. The reduction of oxime was investigated and the 17-amino steroid was obtained via reduction with Ni-Al alloy in yield of 85~90%.Some of target compounds were evaluated for inhibitory activity of 5α-reductase in vitro. In the test for inhibitory activity of rat liver microsomal 5α-reductase, all compounds showed more or less inhibition to rat 5α-reductase. But the inhibitory effects were not well compared with Epristeride.