Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130021, China.
Eur J Med Chem. 2013 Oct;68:385-93. doi: 10.1016/j.ejmech.2013.06.059. Epub 2013 Aug 13.
A cascade operation was designed to synthesize nine coumarin-substituted dihydropyrazoles with only one or two phenolic hydroxyl groups contained. Antioxidant abilities of the obtained compounds were evaluated by inhibiting 2,2'-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu2+/glutathione (GSH)-, and .OH-induced oxidation of DNA. It was found that less phenolic hydroxyl groups can enhance the abilities of coumarin-substituted dihydropyrazoles to protect DNA against the oxidation. Moreover, these coumarin-substituted dihydropyrazoles were employed to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that double phenolic hydroxyl groups were more beneficial for enhancing the abilities of coumarin-substituted dihydropyrazoles to quench the aforementioned radicals. Therefore, dihydropyrazole linked with coumarin exhibited powerful antioxidant effectiveness even in the case of less phenolic hydroxyl groups involved.
设计级联操作来合成含有一个或两个酚羟基的九种香豆素取代的二氢吡唑。通过抑制 2,2'-偶氮双（2-脒基丙烷）盐酸盐（AAPH）、Cu2+/谷胱甘肽（GSH）和·OH 诱导的 DNA 氧化，评估了获得的化合物的抗氧化能力。结果发现，酚羟基较少可以增强香豆素取代的二氢吡唑保护 DNA 免受氧化的能力。此外，这些香豆素取代的二氢吡唑被用于分别清除 2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）阳离子自由基（ABTS+）、2,2'-二苯基-1-苦基肼自由基（DPPH）和半胱氨酸自由基。结果发现，双酚羟基更有利于提高香豆素取代的二氢吡唑清除上述自由基的能力。因此，即使涉及较少的酚羟基，与香豆素相连的二氢吡唑也表现出强大的抗氧化效果。
