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Synthesis, Molecular Structure, Metabolic Stability and QSAR Studies of a Novel Series of Anticancer N-Acylbenzenesulfonamides
Abstract
A series of novel N-acyl-4-chloro-5-methyl-2-(R1-methylthio)benzenesulfonamides 18–47 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.
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Authors (8)
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Beata Żołnowska
- Medical University of Gdańsk Department of Organic Chemistry
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Jarosław Sławiński
- Medical University of Gdańsk Department of Organic Chemistry
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Mariusz Belka
- Medical University of Gdańsk Department of Pharmaceutical Chemistry
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Tomasz Bączek
- Medical University of Gdańsk Department of Pharmaceutical Chemistry
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Anna Kawiak
- Medical University of Gdańsk Department of Human Physiology
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Aneta Pogorzelska
- Medical University of Gdańsk Department of Organic Chemistry
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Krzysztof Szafrański dr
- Medical University of Gdańsk Department of Organic Chemistry
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- Accepted or Published Version
- DOI:
- Digital Object Identifier (open in new tab) 10.3390/molecules201019101
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
MOLECULES
pages 1 - 30,
ISSN: 1420-3049 - Language:
- English
- Publication year:
- 2015
- Bibliographic description:
- 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. -, iss. 20 (2015), s.1-30
- DOI:
- Digital Object Identifier (open in new tab) 10.3390/molecules201019101
- Verified by:
- Gdańsk University of Technology
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