Design, synthesis and antimicrobial evaluation of novel benzoxazole derivatives

• Published in: European journal of medicinal chemistry 2017-01, Vol.126, p.7-14
• Main Authors: Zhang, Wei, Liu, Jingbao, Macho, Jocelyn M., Jiang, Xizhen, Xie, Dongsheng, Jiang, Faqin, Liu, Wenlu, Fu, Lei
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antibacterial activity; Bacillus subtilis - drug effects; Benzoxazole; Benzoxazoles - chemical synthesis; Benzoxazoles - chemistry; Benzoxazoles - pharmacology; Candida albicans - drug effects; Chemistry Techniques, Synthetic; Drug Design; Microbial Sensitivity Tests; Minimum inhibitory concentration; Propanoic acid
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2016.10.010

The synthesis of (S)-2-(4-tert-butylphenoxy)-3-(benzoxazol-5-yl) propanoic acid derivatives (2a-k) were described and their in vitro antibacterial activities were determined against Gram-negative and -positive bacteria. These compounds were found to exert a broad spectrum of activity against the screened bacteria, but poor MIC values were found for Candida albicans fungi. Compound 2b bearing a hydrophobic aromatic tie was the most active derivative against all bacteria studied with MIC values ranging from 0.098 to 0.78 μg/mL. The activity of 2b against B. subtilis was 2-fold higher than Penicillin, and 8- to 510-fold higher than other control antibiotics. Structural modification of lead compound 1a. [Display omitted] •Structural modification of a lead compound 1a was conducted successfully.•General improvement of anti-bacterial activity was observed.•Compound 2b shown excellent activities with MIC = 0.098–0.78 μg/mL.