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Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability
Abstract
A series of new 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives have been synthesized and evaluated in vitro by MTT assays for their antiproliferative activity against cell lines of colon cancer HCT-116, cervical cancer HeLa and breast cancer MCF-7. The obtained results indicated that these compounds display prominent cytotoxic effect. The best anticancer properties have been observed for derivatives 44 (IC50 = 6-18 uM) and 45 (IC50 = 8-14 μM). Very good results of antiproliferative assays have been also shown for compounds 26, 36, and 46 and noticeable anticancer profile has been found for set of derivatives 34e39. Based on results of MTT assays the structure-activity relationships have been drawn. More in-depth biological research revealed that compounds 26, 33, 37, 39, 41 and 43 display cytotoxic effect only against cancer cells and do not inhibit the growth of nonmalignant HaCaT cells. Furthermore, the novel series of derivatives have shown good metabolic stability, especially among the pharmacologically active compounds. To obtain a deeper insight into the molecular description of compounds activity the QSAR studies have been applied. Support vector machines (SVM) have been used to developed QSAR models for predicting the anti-proliferative activity of novel derivatives. The obtained SVM models have shown prognostic ability for HCT-116 and HeLa cell lines and as a result these models may be useful for further development of structurally similar derivatives with better biological properties.
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Authors (9)
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Aneta Pogorzelska
- Medical University of Gdańsk Organic Chemistry
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Jarosław Sławiński
- Medical University of Gdańsk Organic Chemistry
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Beata Żołnowska
- Medical University of Gdańsk Organic Chemistry
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Krzysztof Szafrański dr
- Medical University of Gdańsk Organic Chemistry
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Anna Kawiak
- Międzyuczelniany Wydział Biotechnologii UG i GUMed Wydział Biotechnologii
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Szymon Ulenberg
- Medical University of Gdańsk Pharmaceutical Chemistry
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Joanna Zielińska
- Medical University of Gdańsk Pharmaceutical Chemistry
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Tomasz Bączek
- Medical University of Gdańsk Pharmaceutical Chemistry
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
no. 138,
pages 357 - 370,
ISSN: 0223-5234 - Language:
- English
- Publication year:
- 2017
- Bibliographic description:
- Pogorzelska A., Sławiński J., Żołnowska B., Szafrański K., Kawiak A., Chojnacki J., Ulenberg S., Zielińska J., Bączek T.: Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 138, (2017), s.357-370
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.ejmech.2017.06.059
- Verified by:
- Gdańsk University of Technology
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