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

被引：45

作者：

Lee, H ^{[1
]}

Lee, K

Jung, JK

Cho, J

Theodorakis, EA

机构：

[1] Chungbuk Natl Univ, Coll Pharm, Cheongju 361763, South Korea

[2] Dongguk Univ, Coll Med, Gyeongju 780714, South Korea

[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2005年 / 15卷 / 11期

关键词：

antioxidant; lipid peroxidation; chroman-2-carboxamide;

D O I：

10.1016/j.bmcl.2005.03.118

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2745 / 2748

页数：4

共 18 条

[1]

BRAUGHLER JM, 1986, J BIOL CHEM, V261, P282

[2] BN 80933, a dual inhibitor of neuronal nitric oxide synthase and lipid peroxidation:: A promising neuroprotective strategy [J].

Chabrier, PE ;

Auguet, M ;

Spinnewyn, B ;

Auvin, S ;

Cornet, S ;

Demerlé-Pallardy, C ;

Guilmard-Favre, C ;

Marin, JG ;

Pignol, B ;

Gillard-Roubert, V ;

Roussillot-Charnet, C ;

Schulz, J ;

Viossat, I ;

Bigg, D ;

Moncada, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (19) :10824-10829

[3] Wogonin inhibits excitotoxic and oxidative neuronal damage in primary cultured rat cortical cells [J].

Cho, JS ;

Lee, HK .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2004, 485 (1-3) :105-110

[4] OXIDATIVE STRESS-INDUCED APOPTOSIS PREVENTED BY TROLOX [J].

FORREST, VJ ;

KANG, YH ;

MCCLAIN, DE ;

ROBINSON, DH ;

RAMAKRISHNAN, N .

FREE RADICAL BIOLOGY AND MEDICINE, 1994, 16 (06) :675-684

[5]

Hall E D, 1986, Cent Nerv Syst Trauma, V3, P281

[6]

Hall E. D., 1993, OXYGEN FREE RADICALS, P153

[7]

Halliwell B, 1989, FREE RADICAL BIO MED, P1

[8] Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias [J].

Koufaki, M ;

Detsi, A ;

Theodorou, E ;

Kiziridi, C ;

Calogeropoulou, T ;

Vassilopoulos, A ;

Kourounakis, AP ;

Rekka, E ;

Kourounakis, PN ;

Gaitanaki, C ;

Papazafiri, P .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4835-4841

[9] PROSPECTS FOR THE USE OF ANTIOXIDANT THERAPIES [J].

MAXWELL, SRJ .

DRUGS, 1995, 49 (03) :345-361

[10] Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors [J].

Naderi, GA ;

Asgary, S ;

Ani, M ;

Sarraf-Zadegan, N ;

Safari, MR .

MOLECULAR AND CELLULAR BIOCHEMISTRY, 2004, 267 (1-2) :59-66

← 1 2 →