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Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives
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 M, 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
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Authors (8)
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Beata Żołnowska
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Organicznej
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Jarosław Sławiński
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Organicznej
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Zdzisław Brzozowski
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Organicznej
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Anna Kawiak
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Organicznej
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Mariusz Belka
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Farmacutycznej
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Joanna Zielińska
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Farmacutycznej
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Tomasz Bączek
- Gdański Uniwersytet Medyczny Katedra i Zakład Chemii Farmacutycznej
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
no. 19,
edition 5,
pages 1482 - 1505,
ISSN: 1661-6596 - Language:
- English
- Publication year:
- 2018
- Bibliographic description:
- 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// INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. -Vol. 19, iss. 5 (2018), s.1482-1505
- DOI:
- Digital Object Identifier (open in new tab) 10.3390/ijms19051482
- Verified by:
- Gdańsk University of Technology
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