Abstract
A series of 1,3,4-oxadiazole-2-thiol incorporating fatty acid moieties was synthesized. The chemical structure of the synthesized compounds was established by their spectral data, elemental analysis, and their chemical behavior. Their thioglycosides derivatives and the analogous 1,2,4-triazole were also prepared. The in vitro cytotoxicty of the synthesized compounds was screened against two cell lines; breast cell line MCF-7, and liver cell line HepG2. The most potent compound is (E)-5-(heptadec-8-enyl)-1,3,4-oxadiazole-2-thiol 4f with IC50 (2.82 | µg/ml) and (3.87 µg/ml) against breast cell line MCF-7 and liver cell line HepG2 respectively. Molecular Docking study of Bcl-2 was conducted for the most potent compound, its analogues and the lowest cytotoxicty compound. The antimicrobial activity was also screened, compound (E)-5-ethyl-1,3,4-oxadiazole-2-thiol 4a showed a broad spectrum of activity. A relationship between the length of the fatty acid chain and the biological activity was noticed in the tested compounds.
Keywords: Antifungal, Antimicrobial, Antitumor, Fatty acids, 1, 3, 4-oxadiazole-2-thiol.
Letters in Drug Design & Discovery
Title:Synthesis, Evaluation and Molecular Docking Studies of 1,3,4-oxadiazole- 2-thiol Incorporating Fatty Acid Moiety as Antitumor and Antimicrobial Agents
Volume: 11 Issue: 3
Author(s): Fatma Salah El-Din Mohamed, Ahmed Ismail Hashem, Randa Helmy Swellem and Galal Abd El-Moaen Mohamed Nawwar
Affiliation:
Keywords: Antifungal, Antimicrobial, Antitumor, Fatty acids, 1, 3, 4-oxadiazole-2-thiol.
Abstract: A series of 1,3,4-oxadiazole-2-thiol incorporating fatty acid moieties was synthesized. The chemical structure of the synthesized compounds was established by their spectral data, elemental analysis, and their chemical behavior. Their thioglycosides derivatives and the analogous 1,2,4-triazole were also prepared. The in vitro cytotoxicty of the synthesized compounds was screened against two cell lines; breast cell line MCF-7, and liver cell line HepG2. The most potent compound is (E)-5-(heptadec-8-enyl)-1,3,4-oxadiazole-2-thiol 4f with IC50 (2.82 | µg/ml) and (3.87 µg/ml) against breast cell line MCF-7 and liver cell line HepG2 respectively. Molecular Docking study of Bcl-2 was conducted for the most potent compound, its analogues and the lowest cytotoxicty compound. The antimicrobial activity was also screened, compound (E)-5-ethyl-1,3,4-oxadiazole-2-thiol 4a showed a broad spectrum of activity. A relationship between the length of the fatty acid chain and the biological activity was noticed in the tested compounds.
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Mohamed Salah El-Din Fatma, Hashem Ismail Ahmed, Swellem Helmy Randa and Nawwar Abd El-Moaen Mohamed Galal, Synthesis, Evaluation and Molecular Docking Studies of 1,3,4-oxadiazole- 2-thiol Incorporating Fatty Acid Moiety as Antitumor and Antimicrobial Agents, Letters in Drug Design & Discovery 2014; 11 (3) . https://dx.doi.org/10.2174/157018081131000072
DOI https://dx.doi.org/10.2174/157018081131000072 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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