Synthesis of 7-hydroxy-4-oxo-4H-chromene- and 7-hydroxychroman-2-carboxylic acid N-alkyl amides and their antioxidant activities.
A series of 7-hydroxy-4-oxo-4H-chromene- (3a - h) and 7-hydroxychroman-2-carboxylic acid N-alkyl amides (4a - g) were synthesized and their antioxidant activities were evaluated. While compounds 3a - h were less active, compounds 4a - g exhibited more potent inhibition of lipid peroxidation initiated by Fe2+ and ascorbic acid in rat brain homogenates. Among them, 7-hydroxychroman-2-carboxylic acid N-alkylamides (4e - g) bearing nonyl, decyl, and undecyl side chain exhibited 3 times more potent inhibition than trolox (1).
Kwak
Jae-Hwan
JH
College of Pharmacy, Chungbuk National University, Cheongju, 361-763, Korea.
Kang
Hae-Eun
HE
Jung
Jae-Kyung
JK
Kim
Hwajung
H
Cho
Jungsook
J
Lee
Heesoon
H
D000473:Alkanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D001205:Ascorbic Acid / Q000494:pharmacology; D001713:Biphenyl Compounds; D002839:Chromans / Q000138:chemical synthesis* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000494:pharmacology; D007202:Indicators and Reagents; D007501:Iron / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects; D010851:Picrates / Q000737:chemistry; D051381:Rats
D000473:Alkanes; D000975:Antioxidants; D001713:Biphenyl Compounds; D002839:Chromans; D016166:Free Radical Scavengers; D007202:Indicators and Reagents; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl; D007501:Iron; D001205:Ascorbic Acid; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid