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Assessment of antioxidant potential of selected heterocyclic compounds with coumarin core

Coumarin (2H-1-benzopyran-2-one, 2H-chromen-2- one, 1, 2-benzopyrone) and coumarin derivatives are bioactive phytochemicals that have an important role in the development of anticoagulant, anti-inflammatory, anti-HIV, anticancer and antiviral drugs. Additionally, hydroxycoumarins are very powerful antioxidants that successfully scavenge reactive oxygen species and prevent radical induced biological damage and oxidative stress. The antioxidant potential of 51 heterocyclic compounds containing coumarin core was investigated theoretically. Reaction enthalpies related to two mechanisms of free radical scavenging were calculated. Studied mechanism were hydrogen atom transfer mechanism (HAT) and electron transfer followed by proton transfer mechanism (ET-PT). Calculations were performed using MOPAC2012 COSMO PM7. Cleavage of O–H and N–H bonds was studied. The effect of the position of the hydroxyl group, as well as other functional groups, on the antioxidant activity was examined. Based on obtained results, compounds containing one or more OH– groups exhibit higher radical scavenging properties.

coumarin ; antioxidants ; oxadiazole ; PM7 ; HAT ; ET-PT

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