Isobornylchalcones and flavones derived from them: synthesis and antioxidant activity

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
S. A. Popova, M. V. Krylova, E. V. Pavlova, O. G. Shevchenko, I. Yu. Chukicheva
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引用次数: 0

Abstract

Methoxychalcones containing the NMe2, 3,4-(OMe)2, 3,4,5-(OMe)3, and isobornyl substituents in the B ring were synthesized from 1,3-dihydroxy-4-(1,7,7-trimethylbicyclo-[2.2.1]hept-exo-2-yl)benzene and 1,4-dihydroxy-3-(1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)benzene. Oxidative cyclization of the new isobornylchalcones afforded flavones bearing the 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl moiety. The erythrotoxicity, membrane-protective, and antioxidant activity of the synthesized compounds were evaluated in in vitro models including the model of oxidative hemolysis of mammalian erythrocytes initiated by H2O2 or 2,2′-azobis-(2-amidinopropane) dihydrochloride. All the chalcones studied and most flavones possessed good hemocompatibility and high antioxidant activity. The promise of further research into the synthesis of effective pharmacological substances based on the title compounds was demonstrated.

异冰片基查耳酮及其衍生黄酮:合成与抗氧化活性
在 B 环中含有 NMe2、3,4-(OMe)2、3,4,5-(OMe)3 和异冰片基取代基的甲氧基查耳酮由 1,3-二羟基-4-(1,7,7-三甲基二环-[2.2.1]庚-外-2-基)苯和 1,4-二羟基-3-(1,7,7-三甲基二环[2.2.1]庚-外-2-基)苯合成。新的异冰片查耳酮经氧化环化后得到了具有 1,7,7-三甲基二环[2.2.1]庚-外-2-基分子的黄酮。在体外模型(包括由 H2O2 或 2,2′-偶氮双(2-脒基丙烷)二盐酸盐引发的哺乳动物红细胞氧化溶血模型)中对合成化合物的红细胞毒性、膜保护和抗氧化活性进行了评估。所研究的所有查耳酮和大多数黄酮都具有良好的血液相容性和较高的抗氧化活性。以这些标题化合物为基础合成有效药理物质的进一步研究前景广阔。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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