Departamento de Fisica Aplicada, Centro de Investigacion y de Estudios Avanzados, Unidad Merida, Km 6 Antigua Carretera a Progreso. Apdo. Postal 73, Cordemex, 97310, Merida, Yuc., Mexico.
Unidad de Investigacion Medica Yucatan, Unidad Medica de Alta Especialidad, Centro Medico Ignacio Garcia Tellez, Instituto Mexicano del Seguro Social (IMSS). Calle 41 No. 439 Col. Industrial, 97150, Merida, Yuc., Mexico.
Steroids. 2022 Jul;183:109030. doi: 10.1016/j.steroids.2022.109030. Epub 2022 Mar 30.
The synthesis of a series of 26-amino-22-oxocholestanes derived from diosgenin was accomplished via the substitution of an iodine atom at C-26 by primary and secondary amines. The reactions were conducted in refluxing acetonitrile and through microwave-assisted heating. The latter shows significant improvements in terms of reaction times going from hours to a few minutes or even seconds for completion. Only one of the selected amines, 4-aminourazole, did not yield the substitution product and the imine formation pathway was investigated instead, achieving the 26-iminourazole-22-oxocholestane. All the final products have been characterized and the cytotoxic activity of three of them has been evaluated in SiHa, MCF-7 and MDA tumor cell lines by the sulforhodamine B assay.
通过将碘原子取代甾烷的 C-26 上的初级和二级胺，合成了一系列来源于薯蓣皂素的 26-氨基-22-氧代胆甾烷。反应在回流乙腈中进行，并通过微波辅助加热。后一种方法在反应时间上有显著的改进，从数小时缩短至几分钟甚至几秒钟即可完成。在所选择的胺中，只有一种，即 4-氨基尿嘧啶，没有产生取代产物，而是研究了亚胺形成途径，得到了 26-亚氨基尿嘧啶-22-氧代胆甾烷。所有最终产物都已被表征，并通过磺基罗丹明 B 试验在 SiHa、MCF-7 和 MDA 肿瘤细胞系中评估了其中三种的细胞毒性活性。
