| Autor: |
Mesa D; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Augusto YE; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Hernández G; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Figueroa-Macías JP; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Coll F; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Olea AF; Grupo QBAB, Facultad de Ingeniería, Instituto de Ciencias Químicas Aplicadas, Universidad Autónoma de Chile, Llano Subercaseaux 2801, Santiago 7500912, Chile., Núñez M; Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2390123, Chile., Campo HA; Grupo de Investigación en Procesos Electroquímicos, Departamento de Química, Universidad del Cauca, Calle 5 No. 4-70, Popayán 190003, Colombia., Coll Y; Center for Natural Product Researches, Faculty of Chemistry, University of Havana, Zapata and G, Vedado, Havana 10400, Cuba., Espinoza L; Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2390123, Chile. |
| Abstrakt: |
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. |
