title: Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives.
abstract: Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure-activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 μg/mL.
authors.affiliation: School of Pharmacy, Shanghai Jiao Tong University, Min Hang District, Dong Chuan Road 800, Shanghai 200240, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Wenlu
authors.initials: W
authors.lastname: Liu
authors.forename: Xizhen
authors.initials: X
authors.lastname: Jiang
authors.forename: Faqin
authors.initials: F
authors.lastname: Jiang
authors.forename: Hao
authors.initials: H
authors.lastname: Zhuang
authors.forename: Lei
authors.initials: L
authors.lastname: Fu
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D015195:Drug Design; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000890:Anti-Infective Agents; D011422:Propionates