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Synthesis, biological evaluation, mechanism of action and quantitative structure-activity relationship studies of chalcones as antibacterial agents
Ponnurengan Malliappan Sivakumar,
Published in
2009
PMID: 19291103
Volume: 73
   
Issue: 4
Pages: 403 - 415
Abstract
Forty-eight chalcone analogs were synthesized and their in vitro antibacterial activity against Staphylococcus aureus NCIM 5021, Bacillus subtilis NCIM 2718, Phaseolus vulgaris NCIM 2813, Escherichia coli NCIM 2931, Salmonella typhi 2501 and Enterobacter aerogenes NCIM 5139 were evaluated by microdilution broth assay. Quantitative structure-activity relationships were developed for all the cases (r2 = 0.68-0.79; = 0.58-0.78; q 2 = 0.51-0.68; F = 13.02-61.51). Size, polarizability, electron-donating/withdrawing and hydrophilic nature of the molecule determine the activity against these Gram-positive and Gram-negative bacteria. Staphylococcus aureus was the most and S. typhi was the least hydrophobic of these organisms. These chalcones act better against more hydrophobic organisms. The more active chalcones have log P between 1.5 and 3. Compound 24, one of the most active compounds, was found to act by damaging the cell wall of S. aureus. Slimicidal activity of five of the most active compounds (24, 31, 32, 34 and 37) was found to be in the range of 48-60% against S. aureus and 40-54% against E. coli. A correlation was observed among the hydrophobicity of the compounds, hydrophobicity of the bacterial cell surface and the antibacterial activity of the compound. © 2009 Blackwell Munksgaard.
About the journal
JournalChemical Biology and Drug Design
ISSN17470277
Open AccessNo
Concepts (37)
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    Antiinfective agent
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    Chalcone derivative
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    Antibacterial activity
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    Article
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    Bacillus subtilis
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    Bacterial cell wall
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    Bacterial strain
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    BROTH DILUTION
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    Controlled study
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    Drug mechanism
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    Drug screening
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    Drug synthesis
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    Electron
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    ENTEROBACTER AEROGENES
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    Escherichia coli
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    Hydrophilicity
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    Hydrophobicity
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    In vitro study
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    Molecular size
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    Nonhuman
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    PHASEOLUS VULGARIS
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    Polarization
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    Priority journal
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    Quantitative structure activity relation
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    Salmonella typhi
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    Scanning electron microscopy
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    Staphylococcus aureus
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    Anti-bacterial agents
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    Bacteria
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    Chalcones
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    Microbial viability
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    QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP
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    Bacteria (microorganisms)
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    ENTEROBACTER AEROGENES
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    Negibacteria
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    PHASEOLUS VULGARIS
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    Posibacteria