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Synthesis and QSAR Study of Novel 6-Chloro-3-(2-Arylmethylene-1-methylhydrazino)-1,4,2-benzodithiazine 1,1-Dioxide Derivatives with Anticancer Activity

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Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
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Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, ul. Kładki 24, 80-822 Gdańsk, Poland
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Department of Human Physiology, Medical University of Gdańsk, ul. Tuwima 15, 80-210 Gdańsk, Poland
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Department of Pharmaceutical Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(4), 5754-5770; https://doi.org/10.3390/molecules20045754
Received: 24 February 2015 / Revised: 25 March 2015 / Accepted: 26 March 2015 / Published: 1 April 2015
(This article belongs to the Section Medicinal Chemistry)
A series of new 6-chloro-3-(2-arylmethylene-1-methylhydrazino)-1,4,2-benzodithiazine 1,1-dioxide derivatives were effectively synthesized from N-methyl-N-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)hydrazines. The intermediate compounds as well as the products, were evaluated for their cytotoxic effects toward three human cancer cell lines. All compounds shown moderate or weak cytotoxic effects against the tested cancer cell lines, but selective cytotoxic effects were observed. Compound 16 exhibited the most potent cytotoxic activity against the HeLa cell line, with an IC50 value of 10 µM, while 14 was the most active against the MCF-7 and HCT-116 cell lines, affording IC50 values of 15 µM and 16 µM, respectively. The structure-activity relationship was evaluated based on QSAR methodology. The QSAR MCF-7 model indicated that natural charge on carbon atom C13 and energy of highest occupied molecular orbital (HOMO) are highly involved in cytotoxic activity against MCF-7 cell line. The cytotoxic activity of compounds against HCT-116 cell line is dependent on natural charge on carbon atom C13 and electrostatic charge on nitrogen atom N10. The obtained QSAR models could provide guidelines for further development of novel anticancer agents. View Full-Text
Keywords: sulfonamides; 1,4,2-benzodithiazines; cytotoxic activity; anticancer activity; structure-activity relationship; QSAR; stepwise regression sulfonamides; 1,4,2-benzodithiazines; cytotoxic activity; anticancer activity; structure-activity relationship; QSAR; stepwise regression
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Sławiński, J.; Żołnowska, B.; Brzozowski, Z.; Kawiak, A.; Belka, M.; Bączek, T. Synthesis and QSAR Study of Novel 6-Chloro-3-(2-Arylmethylene-1-methylhydrazino)-1,4,2-benzodithiazine 1,1-Dioxide Derivatives with Anticancer Activity. Molecules 2015, 20, 5754-5770.

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