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Martínez-Gallegos, Anselmo A.; Guerrero-Luna, Gabriel; Ortiz-González, Alejandra; Cárdenas-García, Maura; Bernès, Sylvain; Hernández-Linares, María Guadalupe
Steroids, February 2021, 2021-Feb, 2021-02-00, 20210201, Letnik: 166Journal Article
Display omitted •The 4-azasteroid from diosgenin was prepared in three steps under MW irradiation.•The β-lactam in ring B was achieved from Beckmann rearrangement of the oxime in C-7.•The cytotoxicity test of the azasteroidal compounds showed lower toxicity in LPBH.•Lactam-type enamide derivative shows activity in cancer cell line MDA-MB-231. In this work, we report the synthesis of two new azasteroids through the modification of the A and B rings of diosgenin 1. The 4-azasteroid derivative 12 was prepared in three steps using the α,β-insaturated-3-keto compound 11 as a precursor, which was first oxidized with KMnO4/KIO4 followed by an oxidative cleavage of ring A, and subsequently cyclized with an ammonium salt, under focused microwave irradiation for a short time of 3 min. A second azasteroid was synthesized, for which the key step was the Beckmann rearrangement of ring B of the oxime 16, affording the lactam-type enamide 17 in good yield. The methodologies developed for the synthesis of the precursors derivatives 10 and 11 contribute to improved yields, compared to those reported in the literature. The biological activity of the azasteroidal compounds 12 and 17 and their precursors has been evaluated in cervical cancer cells (HeLa), colon (HCT-15), and triple negative breast cancer (MDA-MB-231) lines.
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