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

ABSTRACT: 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.

SUBMITTER: Mesa D

PROVIDER: S-EPMC10649921 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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

Mesa Dayana D Augusto Yarelys E YE Hernández Giselle G Figueroa-Macías Juan P JP Coll Francisco F Olea Andrés F AF Núñez María M Campo Hernán Astudillo HA Coll Yamilet Y Espinoza Luis L

Molecules (Basel, Switzerland) 20231026 21

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 < ...[more]

PMID: 37959702

Dataset Information

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

Publications

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

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