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Int. J. Mol. Sci. 2018, 19(5), 1482; https://doi.org/10.3390/ijms19051482

Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives

1
Department of Organic Chemistry, Medical University of Gdansk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland
2
Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdansk and Medical University of Gdansk, ul. Abrahama 58, 80-307 Gdansk, Poland
3
Laboratory of Human Physiology, Medical University of Gdansk, ul. Tuwima 15, 80-210 Gdansk, Poland
4
Department of Pharmaceutical Chemistry, Medical University of Gdansk, Al. Gen. J. Hallera 107, 80-416 Gdansk, Poland
5
Department of Inorganic Chemistry, Gdansk University of Technology, ul. Narutowicza 11/12, 80-233 Gdansk, Poland
*
Authors to whom correspondence should be addressed.
Received: 12 April 2018 / Revised: 10 May 2018 / Accepted: 11 May 2018 / Published: 16 May 2018
(This article belongs to the Section Biochemistry, Molecular and Cellular Biology)
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Abstract

A series of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)benzenesulfonamides were synthesized from 4-amino-N-(aryl/heteroaryl)benzenesulfonamides and 2,5-dimethoxytetrahydrofuran. All the synthesized compounds were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. Compound 28, bearing 8-quinolinyl moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 3, 5, and 7 µM, respectively. The apoptotic potential of the most active compound (28) was analyzed through various assays: phosphatidylserine translocation, cell cycle distribution, and caspase activation. Compound 28 promoted cell cycle arrest in G2/M phase in cancer cells, induced caspase activity, and increased the population of apoptotic cells. Relationships between structure and biological activity were determined by the QSAR (quantitative structure activity relationships) method. Analysis of quantitative structure activity relationships allowed us to generate OPLS (Orthogonal Projections to Latent Structure) models with verified predictive ability that point out key molecular descriptors influencing benzenosulfonamide’s activity. View Full-Text
Keywords: benzenesulfonamide; synthesis; anticancer; apoptosis; OPLS benzenesulfonamide; synthesis; anticancer; apoptosis; OPLS
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Żołnowska, B.; Sławiński, J.; Brzozowski, Z.; Kawiak, A.; Belka, M.; Zielińska, J.; Bączek, T.; Chojnacki, J. Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives. Int. J. Mol. Sci. 2018, 19, 1482.

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