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doi:10.1016/j.bmcl.2005.03.118    
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Copyright © 2005 Elsevier Ltd All rights reserved.

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

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Heesoon Leea, Corresponding Author Contact Information, E-mail The Corresponding Author, Keumho Leea, Jae-Kyung Junga, Jungsook Chob and Emmanuel A. Theodorakisc

aCollege of Pharmacy, Chungbuk National University, Cheongju 361-763, Republic of Korea

bCollege of Medicine, Dongguk University, Gyeongju 780-714, Republic of Korea

cDepartment of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0358, USA


Received 1 March 2005; 
revised 28 March 2005; 
accepted 31 March 2005. 
Available online 4 May 2005.

Abstract

A series of 6-hydroxy-7-methoxy-4-chromanone- (2ae) and chroman-2-carboxamides (3ae) were synthesized and their antioxidant activities were evaluated. While compounds 2ae were less active, compounds 3ae 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.

Graphical abstract

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.

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Keywords: Antioxidant; Lipid peroxidation; Chroman-2-carboxamide

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Corresponding Author Contact InformationCorresponding author. Tel.: +82 43 261 2811; fax: +82 43 268 2732

 
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