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DFT and PM7 Study of Radical Inactivation by Selected Heterocyclic Compounds With Coumarin Core

Coumarin (2H-1-benzopyran-2-one, 2H-chromen-2- one, 1, 2-benzopyrone) and coumarine derivatives are polyphenolic compounds widely distributed in plant kingdom and have a great significance as natural fragrances, having a characteristic odour like vanilla beans [1]. These compounds also possess a number of various biological activities, such as anticoagulant, anti- inflammatory, anti-HIV, anticancer, antiviral etc. [2]. Additionally, hydroxycoumarins have been identified as powerful antioxidants that can prevent radical induced damage by scavenging reactive oxygen species [3]. The antioxidative potential of 15 compounds containing coumarin core was investigated theoretically. Reaction enthalpies related to hydrogen atom transfer (HAT) and electron transfer followed by proton transfer (ET-PT) mechanisms were calculated using MOPAC2012 COSMO PM7 and Gaussian 09 DFT/M05-2X/6-311++G(d, p), in conjunction with the SMD continuum solvation model in polar and nonpolar medium [4]. For building QSAR models Dragon and ADMEWorks Programs were used. The effect of the position of the hydroxyl group, as well as other present groups, on the antioxidative activity was examined. Based on the computational results, compounds containing catechol and guaiacol group exhibit the highest radical scavenging properties.

DFT ; PM7 ; coumarin core ; antioxidative potential

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