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Journal of Chemistry
Volume 2017, Article ID 8281518, 7 pages
https://doi.org/10.1155/2017/8281518
Research Article

Synthesis and Antitumor Activity of Novel Pyridoxine-Based Bioisosteric Analogs of trans-Stilbenes

1Kazan (Volga Region) Federal University, Kremlyovskaya 18, Kazan 420008, Russia
2I.M. Sechenov First Moscow State Medical University, Trubetskaya 8, Bldg 2, Moscow 119991, Russia

Correspondence should be addressed to Yurii G. Shtyrlin; moc.liamg@nilryths.iiruy

Received 9 March 2017; Accepted 31 May 2017; Published 6 July 2017

Academic Editor: Ponnurengam Malliappan Sivakumar

Copyright © 2017 Mikhail V. Pugachev et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A series of trans-6-phenylethenyl substituted pyridoxine derivatives, novel bioisosteric analogs of drugs based on trans-stilbene scaffold, were synthesized using the Wittig reaction of a bis-triphenylphosphonium pyridoxine derivative with various aromatic aldehydes. Two compounds demonstrated high activity against the estrogen-dependent MCF-7 (breast cancer) cell line with IC50 in the range of 1.9–7.9 µM and very good selectivity for other studied normal and tumor cells, including the estrogen receptor negative MDA-MB-231 breast cancer cells. The active compounds possessed an intense blue fluorescence, and this feature allowed us to effectively visualize them in cytoplasm and in nucleus. The obtained results make the described chemotype a promising starting point for the development of new anticancer agents for the therapy of estrogen-dependent malignancies.