Solvent-free synthesis of 6β-phenylamino-cholestan-3β,5α-diol and (25R)-6β-phenylaminospirostan-3β,5α-diol as potential antiproliferative agents.

Autor: Soto-Castro D; CONACyT-Instituto Politécnico Nacional, CIIDIR Unidad Oaxaca, Hornos 1003, Santa Cruz Xoxocotlán, Oaxaca C.P. 771230, Mexico., Lara Contreras RC; Departamento de Ingeniería Química-Bioquímica, Instituto Tecnológico de Mérida, Av. Tecnológico S/N, 97118 Mérida, Yucatán, Mexico., Pina-Canseco MDS; Centro de Investigación Facultad de Medicina UNAM-UABJO, Facultad de Medicina y Cirugía, Universidad Autónoma 'Benito Juárez' de Oaxaca, Ex Hacienda de Aguilera S/N, Carretera a San Felipe del Agua, C.P. 68020 Oaxaca, Mexico., Santillán R; Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, México, D.F, Apdo. Postal 14-740, 07000, Mexico., Hernández-Huerta MT; Unidad de Bioquímica e Inmunología, División de Estudios de Posgrado e Investigación, Instituto Tecnológico de Oaxaca, Av. Ing. Víctor Bravo Ahuja #125 esq, Clz. Tecnológico, C.P. 68030 Oaxaca, Mexico., Negrón Silva GE; Departamento de Ciencias Básicas y Departamento de Química, UAM, Av. San Pablo No 180, C.P. 02200 México D.F., Mexico., Pérez-Campos E; Centro de Investigación Facultad de Medicina UNAM-UABJO, Facultad de Medicina y Cirugía, Universidad Autónoma 'Benito Juárez' de Oaxaca, Ex Hacienda de Aguilera S/N, Carretera a San Felipe del Agua, C.P. 68020 Oaxaca, Mexico; Unidad de Bioquímica e Inmunología, División de Estudios de Posgrado e Investigación, Instituto Tecnológico de Oaxaca, Av. Ing. Víctor Bravo Ahuja #125 esq, Clz. Tecnológico, C.P. 68030 Oaxaca, Mexico., Rincón S; Departamento de Ingeniería Química-Bioquímica, Instituto Tecnológico de Mérida, Av. Tecnológico S/N, 97118 Mérida, Yucatán, Mexico. Electronic address: susana74a@yahoo.com.
Jazyk: angličtina
Zdroj: Steroids [Steroids] 2017 Oct; Vol. 126, pp. 92-100. Date of Electronic Publication: 2017 Aug 18.
DOI: 10.1016/j.steroids.2017.08.008
Abstrakt: In this paper is described a synthetic route to 6β-phenylamino-cholestan-3β,5α-diol and (25R)-6β-phenylaminospirostan-3β,5α-diol, starting from cholesterol and diosgenin, respectively. The products were obtained in two steps by epoxidation followed by aminolysis, through an environmentally friendly and solvent-free method mediated by SZ (sulfated zirconia) as catalyst. The use of SZ allows chemo- and regioselective ring opening of the 5,6α-epoxide during the aminolysis reaction eliminating the required separation of the epoxide mixture. The products obtained were spectroscopically characterized by 1 H, PENDANT 13 C NMR and HETCOR experiments, and complemented with FTIR-ATR and HRMS. The antiproliferative effect of the β-aminoalcohols was evaluated on MCF-7 cells after 48h of incubation, by MTT and CVS assays. These methodologies showed that both compounds have antiproliferative activity, being more active the cholesterol analogue. Additionally, the cell images obtained by Harris' Hematoxylin and Eosin (H&E) staining protocol, evidenced formation of apoptotic bodies due to the presence of the obtained β-aminoalcohols in a dose-dependent manner.
(Copyright © 2017. Published by Elsevier Inc.)
Databáze: MEDLINE
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