Abstract:
:Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of these compounds, 3-(4-bromophenyl)-4-(2-(4-nitrophenyl)hydrazinyl)furan-2(5H)-one (4a11) showed the most potent antibacterial activity against S. aureus ATCC 25923 with MIC(50) of 0.42 μg/mL. The enzyme assay revealed that the possible antibacterial mechanism of the synthetic compounds might be due to their inhibitory activity against tyrosyl-tRNA synthetase. Molecular dockings of 4a11 into S. aureus tyrosyl-tRNA synthetase active site were also performed. This inhibitor snugly fitting the active site might well explain its excellent inhibitory activity. Meanwhile, this modeling disclosed that a more suitable optimization strategy might be to modify the benzene ring at 3-position of furanone with hydrophilic groups.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HLdoi
10.1016/j.bmc.2011.01.051subject
Has Abstractpub_date
2011-03-01 00:00:00pages
1571-9issue
5eissn
0968-0896issn
1464-3391pii
S0968-0896(11)00080-0journal_volume
19pub_type
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