title: Synthesis and biological evaluation of a series of 2-(substitutedphenyl)benzothiazoles.
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 (1)H-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 (IC(50), 10.07-13.21 μg/ml). Brominated and nitrated derivatives (1k, 1l, respectively) of 1e exhibited even more potent cytotoxicity.
authors.affiliation: Department of Pharmaceutical Chemistry, Hanoi University of Pharmacy, 13-15 Le Thanh Tong, Hanoi, Vietnam. nhnam@etal.uri.edu
authors.forename: Nguyen Hai
authors.initials: NH
authors.lastname: Nam
authors.forename: Phan Thi Phuong
authors.initials: PT
authors.lastname: Dung
authors.forename: Phuong Thien
authors.initials: PT
authors.lastname: Thuong
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D052160:Benzothiazoles