title: Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA.
abstract: A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+•) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c exhibited the termination of radical propagation-chains in AAPH-induced oxidation of DNA. The ortho dihydroxyphenyl substitution at 5 position and 1-unsubstitution of the 4,5-dihydroxylpyrazole was found enhancing the antioxidant activities of these coumarin derivatives.
authors.affiliation: Department of Organic Chemistry, College of Chemistry, Jilin University, No 2699 Qianjin Road, Changchun 130012, China.
authors.forename: Chuan
authors.initials: C
authors.lastname: Xiao
authors.forename: Xu-Yang
authors.initials: XY
authors.lastname: Luo
authors.forename: De-Jun
authors.initials: DJ
authors.lastname: Li
authors.forename: Hang
authors.initials: H
authors.lastname: Lu
authors.forename: Zai-Qun
authors.initials: ZQ
authors.lastname: Liu
authors.forename: Zhi-Guang
authors.initials: ZG
authors.lastname: Song
authors.forename: Ying-Hua
authors.initials: YH
authors.lastname: Jin
mesh_terms: D000578:Amidines / Q000494:pharmacology; D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction / Q000187:drug effects; D010851:Picrates / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry
chemical_list: D000578:Amidines; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D003374:Coumarins; D016166:Free Radical Scavengers; D010851:Picrates; D011720:Pyrazoles; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C046728:2,2'-azobis(2-amidinopropane); D004247:DNA; C004931:1,1-diphenyl-2-picrylhydrazyl