Design, synthesis and antimicrobial evaluation of novel benzoxazole derivatives

Wei Zhang; Jingbao Liu; Jocelyn M Macho; Xizhen Jiang; Dongsheng Xie; Faqin Jiang; Wenlu Liu; Lei Fu

doi:10.1016/j.ejmech.2016.10.010

Design, synthesis and antimicrobial evaluation of novel benzoxazole derivatives

Eur J Med Chem. 2017 Jan 27:126:7-14. doi: 10.1016/j.ejmech.2016.10.010. Epub 2016 Oct 6.

Authors

Wei Zhang¹, Jingbao Liu², Jocelyn M Macho³, Xizhen Jiang², Dongsheng Xie², Faqin Jiang², Wenlu Liu⁴, Lei Fu⁵

Affiliations

¹ School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd., Shanghai 200240, China; Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA.
² School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd., Shanghai 200240, China.
³ Department of Chemistry, University of Florida, Gainesville, FL, 32611-7200, USA.
⁴ School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd., Shanghai 200240, China. Electronic address: sdwenlu@sjtu.edu.cn.
⁵ School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Rd., Shanghai 200240, China. Electronic address: leifu@sjtu.edu.cn.

PMID: 27744188
DOI: 10.1016/j.ejmech.2016.10.010

Abstract

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.

Keywords: Antibacterial activity; Benzoxazole; Minimum inhibitory concentration; Propanoic acid.

MeSH terms

Anti-Infective Agents / chemical synthesis*
Anti-Infective Agents / chemistry
Anti-Infective Agents / pharmacology*
Bacillus subtilis / drug effects
Benzoxazoles / chemical synthesis*
Benzoxazoles / chemistry
Benzoxazoles / pharmacology*
Candida albicans / drug effects
Chemistry Techniques, Synthetic
Drug Design*
Microbial Sensitivity Tests

Substances

Anti-Infective Agents
Benzoxazoles