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Molecules 2015, 20(10), 19101-19129; doi:10.3390/molecules201019101

Synthesis, Molecular Structure, Metabolic Stability and QSAR Studies of a Novel Series of Anticancer N-Acylbenzenesulfonamides

1
Department of Organic Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
2
Department of Pharmaceutical Chemistry, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland
3
Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, ul. Kładki 24, 80-822 Gdańsk, Poland
4
Department of Human Physiology, Medical University of Gdańsk, ul. Tuwima 15, 80-210 Gdańsk, Poland
5
Department of Inorganic Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80-233 Gdańsk, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Dimitra Hadjipavlou-Litina
Received: 9 September 2015 / Revised: 1 October 2015 / Accepted: 12 October 2015 / Published: 21 October 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1304 KB, uploaded 23 October 2015]   |  

Abstract

A series of novel N-acyl-4-chloro-5-methyl-2-(R1-methylthio)benzenesulfonamides 1847 have been synthesized by the reaction of N-[4-chloro-5-methyl-2-(R1-methylthio) benzenesulfonyl]cyanamide potassium salts with appropriate carboxylic acids. Some of them showed anticancer activity toward the human cancer cell lines MCF-7, HCT-116 and HeLa, with the growth percentages (GPs) in the range from 7% to 46%. Quantitative structure-activity relationship (QSAR) studies on the cytotoxic activity of N-acylsulfonamides toward MCF-7, HCT-116 and HeLa were performed by using topological, ring and charge descriptors based on the stepwise multiple linear regression technique (MLR). The QSAR studies revealed three predictive and statistically significant models for the investigated compounds. The results obtained with these models indicated that the anticancer activity of N-acylsulfonamides depends on topological distances, number of ring system, maximum positive charge and number of atom-centered fragments. The metabolic stability of the selected compounds had been evaluated on pooled human liver microsomes and NADPH, both R1 and R2 substituents of the N-acylsulfonamides simultaneously affected them. View Full-Text
Keywords: sulfonamide; synthesis; anticancer; QSAR; metabolic stability sulfonamide; synthesis; anticancer; QSAR; metabolic stability
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MDPI and ACS Style

Żołnowska, B.; Sławiński, J.; Belka, M.; Bączek, T.; Kawiak, A.; Chojnacki, J.; Pogorzelska, A.; Szafrański, K. Synthesis, Molecular Structure, Metabolic Stability and QSAR Studies of a Novel Series of Anticancer N-Acylbenzenesulfonamides. Molecules 2015, 20, 19101-19129.

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