Synthesis and evaluation of 6-hydroxy-7-methoxy-4-chromanone- and chroman-2-carboxamides as antioxidants

A series of 6-hydroxy-7-methoxy-4-chromanone- (2a–e) and chroman-2-carboxamides (3a–e) were synthesized and their antioxidant activities were evaluated. While compounds 2a–e were less active, compounds 3a–e exhibited more potent inhibition of lipid peroxidation initiated by Fe2+ and ascorbic acid in rat brain homogenates. Among them, N-arylsubstituted-chroman-2-carboxamides (3d and 3e) exhibited 25–40 times more potent inhibition than trolox (1). The DPPH radical scavenging activity of compound 3d was comparable to that of trolox.

A series of 6-hydroxy-7-methoxy-4-chromanone- and chroman-2-carboxamides were synthesized and their antioxidant activities were evaluated. The most active compounds 3d and 3e exhibited 25–40 times more potent inhibition of lipid peroxidation than trolox in rat brain homogenates.Figure optionsDownload as PowerPoint slide