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Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Synthesis and Biological Evaluation of a Series of 2-(Substitutedphenyl) benzothiazoles

Author(s): Nguyen Hai Nam, Phan Thi Phuong Dung and Phuong Thien Thuong

Volume 7, Issue 2, 2011

Page: [127 - 134] Pages: 8

DOI: 10.2174/157340611794859361

Price: $65

Abstract

A series of 2-phenylbenzothiazoles has been synthesized either by i) condensation of different aromatic aldehydes with 2-aminothiophenol or ii) condensation of N-(2-chlorophenyl)benzothioamides in KOH catalyzed by potassium fericyanide. The structures of synthesized compounds were confirmed by IR, MS, and 1H-NMR. The results of biological activity screening showed that six compounds including 2-phenylbenzothiazol (1a), 2-(2-chlorophenyl)benzothiazole (1b), 2- (3-chlorophenyl)benzothiazole (1c), 2-(4-hydroxyphenyl)benzothiazole (1e), 2-(4-dimethylaminophenyl)benzothiazole (1h) and 2-(2,3,4-trimethoxyphenyl)benzothiazole (1i) exhibited significant antibacterial activities; two compounds (1a, 1e) exhibited antifungal activities. Especially, 1e showed considerable antimicrobial activity against both A. niger and F. oxysporum. The brominated derivative of 1e displayed extended spectrum against all four bacterial strains tested with lower MIC values. In vitro cytotoxicity of the synthesized compounds was evaluated on three cancer cell lines (A549, HT1080, MCF7-MDR). The results indicated that three compounds (1e, 1g, 1i) exhibited significant cytotoxic activity on A549 and MCF7-ADR cells (IC50, 10.07-13.21μg/ml). Brominated and nitrated derivatives (1k, 1l, respectively) of 1e exhibited even more potent cytotoxicity.

Keywords: 2-Phenylbenzothiazole, synthesis, cytotoxicity, antibacterial, antifungal, condensation, aromatic aldehydes, antimicrobial, IR, MS, 1H-NMR


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