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. 2016 Mar 10;21(3):340.
doi: 10.3390/molecules21030340.

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Xiaoqin Wang  1 , Xiaoyang Xie  2 , Yuanhong Cai  3 , Xiaolan Yang  4 , Jiayu Li  5 , Yinghan Li  6 , Wenna Chen  7 , Minghua He  8
Affiliations

Design, Synthesis and Antibacterial Evaluation of Some New 2-Phenyl-quinoline-4-carboxylic Acid Derivatives

Xiaoqin Wang et al. Molecules. .

Abstract

A series of new 2-phenyl-quinoline-4-carboxylic acid derivatives was synthesized starting from aniline, 2-nitrobenzaldehyde, pyruvic acid followed by Doebner reaction, amidation, reduction, acylation and amination. All of the newly-synthesized compounds were characterized by ¹H-NMR, (13)C-NMR and HRMS. The antibacterial activities of these compounds against Gram-negative (Escherichia coli, Pseudomonas aeruginosa) and Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis), as well as one strain of methicillin-resistant Staphylococcus aureus (MRSA) bacteria were evaluated by the agar diffusion method (zone of inhibition) and a broth dilution method (minimum inhibitory concentration (MIC)), and their structure-activity relationships were obtained and discussed. The results revealed that some compounds displayed good antibacterial activity against Staphylococcus aureus, and Compounds 5a₄ and 5a₇ showed the best inhibition with an MIC value of 64 μg/mL against Staphylococcus aureus and with an MIC value of 128 μg/mL against Escherichia coli, respectively. The results of the MTT assay illustrated the low cytotoxicity of Compound 5a4.

Keywords: 2-phenyl-quinoline-4-carboxylic acid derivatives; Doebner reaction; antibacterial activity; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The structures of 2-aryl-quinoline-4-carboxylic acid derivatives with antimicrobial activities.
Scheme 1
Scheme 1
Synthetic route of 2-phenyl-quinoline-4-carboxylic acid derivatives.
See this image and copyright information in PMC

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