Design of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Milan MladenovićSlavica Solujić

Abstract

This paper presents the design of novel 4-hydroxy-chromene-2 one derivatives, based on previously obtained minimal inhibitory concentration values (MICs), against twenty four microorganism cultures, gram positive and negative bacteria and fungi. Two of our compounds, 3b (MIC range 130-500 microg/mL) and 9c (31.25-62.5 microg/mL), presented high potential antimicrobial activity. The compound 9c had equal activity to the standard ketoconazole (31.25 microg/mL) against M. mucedo. Enlarged resistance of S. aureus, E. coli and C. albicans on the effect of potential drugs and known toxicity of coumarin antibiotics, motivated us to establish SAR and QSAR models of activity against these cultures and correlate biological activity, molecular descriptors and partial charges of functional groups to explain activity and use for the design of new compounds. The QSAR study presents essential relation of antimicrobial activity and dominant substituents, 4-hydroxy, 3-acetyl and thiazole functional groups, also confirmed through molecular docking. The result was ten new designed compounds with much improved predicted inhibition constants and average biological activity.

References

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Mar 4, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Adriana BasileSergio Rosselli
Apr 23, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Milan MladenovićSlavica Solujić
Aug 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jaroslaw WidelskiIoanna Chinou

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Citations

Jan 12, 2013·International Journal of Molecular Sciences·Rodrigo S A de AraújoJosé M Barbosa-Filho
Jul 11, 2012·Journal of Biochemical and Molecular Toxicology·Sanja MatićVladimir Mihailović
Mar 18, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Maria Concetta GidaroSimone Carradori
Jan 10, 2013·Journal of Pharmaceutical and Biomedical Analysis·Marina IlijašVišnja Stepanić
Oct 30, 2019·Mini Reviews in Medicinal Chemistry·Navjot Singh SethiRajesh K Singh

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Methods Mentioned

BETA
infrared spectroscopy

Software Mentioned

ChemOffice
MacroModel
VegaZZ
Spartan
MOPAC PM6
Chimera
CS Gaussian
AutoDock
Origin Pro
Chem3D Ultra

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