The Synthesis of Novel aza -Steroids and α , β -Unsaturated-Cyanoketone from Diosgenin.

Recent studies have demonstrated the antiproliferative and cytotoxic effects of aza-steroids and steroidal sapogenins on human cancer cell lines. The scientific community has shown a growing interest in these compounds as drug candidates for cancer treatment. In the current work, we report the synthesis of new diosgenin oxime derivatives as potential antiproliferative agents. From (25 R )-5α-spirost-3,5,6-triol ( 1 ), a diosgenin derivative, ketones 2 , 3 , 4, and 9 were obtained and used as precursors of the new oximes. A condensation reaction was carried out between the steroidal ketones ( 2 , 3 , 4 , and 9 ) with hydroxylamine hydrochloride in 2,4,6-trimethylpyridine to produce five spirostanic oximes (four of them are not reported before) with a 42-96% yield. Also, a new spirostanic α , β -unsaturated cyanoketone was synthesized via Beckmann fragmentation using thionyl chloride with a 62% yield. Furthermore, we proposed a reaction mechanism with the aim of explaining such transformation.