Molecules, Vol. 28, Pages 7283: The Synthesis of Novel aza-Steroids and & alpha;, & beta;-Unsaturated-Cyanoketone from Diosgenin

Molecules, Vol. 28, Pages 7283: The Synthesis of Novel aza-Steroids and α, β-Unsaturated-Cyanoketone from Diosgenin Molecules doi: 10.3390/molecules28217283 Authors: Dayana Mesa Yarelys E. Augusto Giselle Hernández Juan P. Figueroa-Macías Francisco Coll Andrés F. Olea María Núñez Hernán Astudillo Campo Yamilet Coll Luis Espinoza 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.
Source: Molecules - Category: Chemistry Authors: Tags: Article Source Type: research