Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
Eur J Med Chem. 2010 May;45(5):1821-7. doi: 10.1016/j.ejmech.2010.01.018. Epub 2010 Jan 20.
5,7-, 5,8-, 6,8-, 7,8-dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2'-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl radicals. 6,8-DCQA possessed the highest efficacy to protect methyl linoleate against 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced oxidation. 5,7-, 5,8-DCQA and QA were able to retard the beta-carotene-bleaching in beta-carotene-linoleic acid emulsion. In addition, 5,8- and 6,8-DCQA efficiently protected DNA against hydroxyl radical (.OH)-mediated oxidation, and 5,8-DCQA and 7-CQA were active to protect DNA against AAPH-induced oxidation. Furthermore, only 7-CQA can protect DNA against Cu2+/glutathione (GSH)-mediated oxidation. Dichloro-4-quinolinol-3-carboxylic acids were potent to be antiradical drugs, and were worthy to be researched pharmacologically.
5,7-, 5,8-, 6,8-, 7,8-二氯-4-喹啉羧酸（5,7-, 5,8-, 6,8-, 7,8-DCQA）与 7-氯-4-喹啉羧酸（7-CQA）和 4-喹啉羧酸（QA）一起合成，以研究其抗氧化性能。5,7-DCQA 表现出最强的清除 2,2'-联氮双（3-乙基苯并噻唑啉-6-磺酸）阳离子自由基（ABTS+）、2,2'-二苯基-1-苦基肼（DPPH）和 galvinoxyl 自由基的能力。6,8-DCQA 具有最高的功效，可保护甲基亚油酸酯免受 2,2'-偶氮双（2-脒基丙烷）二盐酸盐（AAPH）诱导的氧化。5,7-、5,8-DCQA 和 QA 能够延缓β-胡萝卜素-亚油酸乳液中的β-胡萝卜素漂白。此外，5,8-和 6,8-DCQA 有效地保护 DNA 免受羟基自由基（.OH）介导的氧化，5,8-DCQA 和 7-CQA 对保护 DNA 免受 AAPH 诱导的氧化具有活性。此外，只有 7-CQA 可以保护 DNA 免受 Cu2+/谷胱甘肽（GSH）介导的氧化。二氯-4-喹啉羧酸是有效的自由基清除药物，值得进行药理学研究。
