Synthesis, antibacterial activities, and theoretical studies of dicoumarols

Four dicoumarols (DC, 2-PyDC, 3-PyDC and 4-PyDC) were synthesized and characterized via IR, (1)H NMR, HRMS, and single crystal X-ray crystallography. Two classical intramolecular O-H···O hydrogen bonds (HBs) stabilized their structures. The total HB energies in DC, 2-PyDC, 3-PyDC and 4-PyDC were cal...

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Published in:Organic & biomolecular chemistry 2014-08, Vol.12 (29), p.5528-5535
Main Authors: Li, Jing, Hou, Zheng, Chen, Guang-Hui, Li, Fen, Zhou, Ying, Xue, Xiao-Yan, Li, Zhou-Peng, Jia, Min, Zhang, Zi-Dan, Li, Ming-Kai, Luo, Xiao-Xing
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Anti-Bacterial Agents - toxicity
Cell Death
Crystallography, X-Ray
Dicumarol - chemical synthesis
Dicumarol - chemistry
Dicumarol - pharmacology
Dicumarol - toxicity
Electrons
Human Umbilical Vein Endothelial Cells - cytology
Human Umbilical Vein Endothelial Cells - drug effects
Hydrogen Bonding
Methicillin-Resistant Staphylococcus aureus - drug effects
Methicillin-Resistant Staphylococcus aureus - growth & development
Microbial Sensitivity Tests
Models, Molecular
Quantum Theory
Staphylococcus
Static Electricity
Thermodynamics
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Summary:Four dicoumarols (DC, 2-PyDC, 3-PyDC and 4-PyDC) were synthesized and characterized via IR, (1)H NMR, HRMS, and single crystal X-ray crystallography. Two classical intramolecular O-H···O hydrogen bonds (HBs) stabilized their structures. The total HB energies in DC, 2-PyDC, 3-PyDC and 4-PyDC were calculated with the density functional theory (DFT) [B3LYP/6-31G*] method. The in vitro antibacterial activity of DC, 2-PyDC, 3-PyDC and 4-PyDC against Staphylococcus aureus (S. aureus ATCC 29213), methicillin-resistant S. aureus (MRSA XJ 75302), vancomycin-intermediate S. aureus (Mu50 ATCC 700699), and USA 300 (Los Angeles County clone, LAC) was evaluated by observing the minimum inhibitory concentration and time-kill curves. The results showed that among all the compounds, 2-PyDC exhibited the most potent antibacterial activity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00772g