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 Fe(2+) 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.
Lee
Heesoon
H
College of Pharmacy, Chungbuk National University, Cheongju, Republic of Korea. medchen@chungbuk.ac.kr
Lee
Keumho
K
Jung
Jae-Kyung
JK
Cho
Jungsook
J
Theodorakis
Emmanuel A
EA
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002867:Chromones
D000880:Anthraquinones; D000975:Antioxidants; D002839:Chromans; D002867:Chromones; C469373:chaetomanone