Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 23, Issue 20, Pages 6602-6611Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2015.09.018
Keywords
Adenosine analogs; Tyrosyl-tRNA synthetase inhibitors; Antibacterial; Molecular docking
Funding
- National Natural Science Foundation of China [21262013]
- Hunan Provincial Natural Science Foundation of China [2015JJ2116]
- Jishou University [14JDY053]
- Specialty Plant Resources Development and Utilization of Wuling Mountain in Innovation Base for the Graduate Student Training of Hunan Provincial [2014KFXM04]
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Herein we describe the synthesis and evaluation of a series of adenosine analogs for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Out of these compounds, compound c6 has much stronger antibacterial potency against Pseudomonas aeruginosa than ciprofloxacin, and was determined to target tyrosyl-tRNA synthetase with IC50 zof 0.8 +/- 0.07 mu M. Structure-activity relationship analysis suggested that introduction of a fluorine atom at the 3'-position of benzene ring of the phenylacetyl moiety significantly increased affinities to the enzyme. In comparison with isopropylidene analogs, 2',3'-deprotected compounds displayed higher inhibitory activity. Molecular dockings provided an explanation for observations in biological assays. (c) 2015 Elsevier Ltd. All rights reserved.
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