Heterocyclic derivatives with 2,4-dihydroxyphenyl moiety are  compounds of documented in vitro and in vivo anticancer activity [1]. We reported the synthesis and antiproliferative activity of 1,3,4-thiadiazoles, 4H-3,1-benzothiazines and benzimidazoles [2]. Taking into account their valuable biological properties we developed an efficient synthesis of novel differently substituted thieno[1,3]thiazin-4-ones. We obtained a series of compounds modified at positions 3 and 5 of a resorcinol moiety to find the most active structures.
The compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with a corresponding aminothiophenecarboxamides. Their structures were identified using elemental, IR, ¹H NMR, ¹³C NMR and mass spectra analyses. The developed method offers short reaction times, relatively large-scale synthesis, easy and quick isolation of the products, and good yields.

Figure

Compounds in Figure were evaluated for their antiproliferative activity against human non-small cells lung cancer (A549), human colon adenocarcinoma (HT-29) and rat glioma (C6) cells. Cisplatin was used as a reference drug. For comparison, cytotoxicity of compounds was determined in normal human skin fibroblast (HSF) primary culture with use LDH method.
Proliferation of all tested cancer cells was decreased in the cultures exposed to a compounds in a concentration-dependent fashion as measured by means of MTT assay. The activities of compounds were varied and evidently depended on the type of substitution on both rings.

This study was supported by the National Science Centre (Poland), decision No. DEC-2011/01/B/NZ4/05005.

References:

1. McDonald E., Jones K., et. al. Curr. Top. Med. Chem. 6, 1193 (2006).

2. Rzeski W., Matysiak J., et. al.  Bioorg. Med. Chem., 15, 3201 (2007).

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/31106 must be provided.

1. Synthesis and biological activity of novel N,N-cyclic-2,4-dihydroxythiobenzamide derivatives