Synthesis of new coumarin[1,3]oxazine derivatives of 7-hydroxy-6-isobornyl-4-methylcoumarin and their antioxidant activity

Abstract

In this work, we synthesized a series of new 9,10-dihydro-2H,8H-chromeno[8,7e][1,3]oxazine-2-on derivatives which incorporate isobornylcoumarin and 1,3-oxazine moieties. A structure-antioxidant activity relationship was analyzed. A comparative evaluation of their radical scavenging activity, antioxidant and membrane-protective properties was carried out in test with DPPH, as well as on the models of Fe²⁺ /ascorbate-initiated lipid peroxidation and oxidative hemolysis of mammalian red blood cells. The results suggest that all the obtained coumarin[1,3]oxazine derivatives of 7-hydroxy-6-isobornyl-4-methylcoumarin are capable of exhibiting antioxidant activity in various model systems. Compound 7 with a phenyl fragment, combining high radical scavenging activity and the ability to inhibit Fe²⁺ /ascorbate-initiated peroxidation of animal lipids in a heterogeneous environment, also proved to be the most effective membrane protector and antioxidant in the model of H₂ O₂ -induced erythrocyte hemolysis.

Keywords: 1,3-oxazine derivatives; antioxidant activity; coumarin; isobornylphenol; membrane-protective activity; oxidative hemolysis; radical scavenging activity; terpenophenols.