Design and synthesis of coumarin-3-acylamino derivatives to scavenge radicals and to protect DNA

Abstract

In this study, a series of coumarin-3-acylamino derivatives containing phenethylamine moiety or tyramine moiety were synthesized and their antioxidant activities were evaluated by Cu(2+)/glutathione(GSH)-, ˙OH- and 2,2'-azobis(2-amidinopropane hydrochloride)(AAPH)-induced oxidation of DNA. It was found that both hydroxyl and ortho-methoxy groups at A ring, hydroxyl group at B ring and peptide bond can enhance the abilities of coumarin-3-acylamino derivatives to protect DNA against ˙OH- and AAPH-induced oxidation. Moreover, these coumarin-3-acylamino derivatives were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+˙)). We found that tyramine moiety, hydroxyl and ortho-methoxy are the key groups to enhance the activities of antioxidants to quench ABTS(+˙). Therefore, tyramine linked with coumarin-3-carboxyl acid which containing hydroxyl and ortho-methoxy exhibited powerful antioxidant abilities.

Keywords: Antioxidant; Coumarin; Coumarin-3-acylamino; DNA; Free radical; Oxidation.