Synthesis of New Bicyclic Hydroxamic Acids with Cytotoxic Activity

Iker S. Escalona-Torres, Francisco Yuste, Rubén Sánchez-Obregón

Abstract


Six new bicyclic hydroxamic acids were synthesized through an uncommon nitro group rearrangement between β-nitrostyrenes and dimedone. The structures of all the new synthesized compounds were confirmed using a combination of FTIR, 1H NMR, 13C NMR and mass spectral data. Likewise, the cytotoxic activity of the obtained products was evaluated in six different cancer cell lines. Two compounds showed significant potency on two cancer cell lines with IC50 between 9.31±0.1 and 23.38±0.9 μM.

Keywords


Hydroxamic acids; Michael addition; nitro group rearrangement; cytotoxic activity

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DOI: http://dx.doi.org/10.29356/jmcs.v61i4.467

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Copyright (c) 2018 Iker S. Escalona-Torres, Francisco Yuste, Rubén Sánchez-Obregón

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Vol 62, No 2 (2018). Quarterly publication (April-June). Edited and distributed by Sociedad Química de México, A.C. Barranca del Muerto 26, Col. Crédito Constructor, Del. Benito Juárez, C.P. 03940, Mexico City. Phone: +5255 56626837; +5255 56626823 Contact: soquimex@sqm.org.mx http://www.sqm.org.mx Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2005-052710530600-102. Certificate of lawful title and content: Under procedure. ISSN-e granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 2594-0317. ISSN granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 1870-249X. Postal registration of printed matter deposited by editors or agents granted by SEPOMEX: IM09-0312 Copyright © Sociedad Química de México, A.C. Total or partial reproduction is prohibited without written permission of the right holder. The Figures/schemes quality and the general contents of this publication are full responsibility of the authors. Updated June 6th, 2018 by Adriana Vázquez (editorial assistant, e-mail: editor.jmcs@gmail.com), J. Mex. Chem. Soc., Sociedad Química de México, A.C.