Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 46, Issue 10, Pages 4904-4914Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2011.07.047
Keywords
3-Aryl-4-arylaminofuran-2(5H)-one; Antibacterial agent; Molecular docking; Tyrosyl-tRNA synthetase; Structure-activity relationship
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Funding
- Hunan Provincial Natural Science Foundation of China [11JJ3113]
- Key Laboratory of Plant Resources Conservation and Utilization (Jishou University), College of Hunan Province [JSK 201106]
- Key Laboratory of Hunan Forest Products and Chemical Industry Engineering of Hunan Province [JDZ201102]
- Key Laboratory of Ecotourism's Application Technology, Hunan Province [JDSTLY 01103]
- program for Science and Technology Innovative Research Team (Chemicals of Forestry Resources and Development of Forest Products) in Higher Educational Institutions of Hunan Province
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Thirty-five 3-aryl-4-arylaminofuran-2(5H)-one derivatives were designed, prepared and tested for their inhibitory activity against tyrosyl-tRNA synthetase. Out of these compounds, 3-(3-bromophenyl)-4-(3,5-dichlorophenylamino)furan-2(5H)-one (35) was the most active with IC50 of 0.09 +/- 0.02 mu M. The structure activity relationship revealed that introduction of chlorine atoms at both meta positions of aniline moiety significantly increased the enzyme inhibitory activity. The results of antibacterial assay revealed that the tested compounds showed good activity against Gram-positive bacteria, with 35 being the most potent with MIC50 of 0.06 mu g/mL against Staphylococcus aureus ATCC 25923. Molecular docking of 35 into S. aureus tyrosyl-tRNA synthetase active site was also performed. The inhibitor snugly fitting the active site may well explain its excellent inhibitory activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
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