title: Synthesis and antioxidant activity of novel Mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan.
abstract: A new series of Mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan (6a-6ae) were synthesized and characterized by (1)H NMR, ESI-MS and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction. All these novel compounds were screened for their in vitro antioxidant activity employing 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+)) and ferric reducing antioxidant power (FRAP) scavenging assays. Due to the combination of 1,4-benzodioxan, 1,3,4-oxadiazoles and substituted phenyl ring, most of them exhibited nice antioxidant activities. In all of these three assays mentioned above, compounds 6f and 6e showed significant radical scavenging ability comparable to the commonly used antioxidants, BHT and Trolox. Seven compounds with representative substituents or activities were selected for further assays in chemical simulation biological systems-inhibition of microsomal lipid peroxidation (LPO) and protection against 2,2'-azobis (2-amidinopropane hydrochloride) (AAPH) induced DNA strand breakage, in which, 6f and 6e were demonstrated to be of the most potent antioxidant activities.
authors.affiliation: College of Plant Protection, Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Liang
authors.initials: L
authors.lastname: Ma
authors.forename: Yu
authors.initials: Y
authors.lastname: Xiao
authors.forename: Cong
authors.initials: C
authors.lastname: Li
authors.forename: Zheng-Lu
authors.initials: ZL
authors.lastname: Xie
authors.forename: Dong-Dong
authors.initials: DD
authors.lastname: Li
authors.forename: Yan-Ting
authors.initials: YT
authors.lastname: Wang
authors.forename: Hai-Tian
authors.initials: HT
authors.lastname: Ma
authors.forename: Hai-Liang
authors.initials: HL
authors.lastname: Zhu
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Wang
authors.forename: Yong-Hao
authors.initials: YH
authors.lastname: Ye
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D053903:DNA Breaks, Double-Stranded / Q000187:drug effects; D004146:Dioxanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015227:Lipid Peroxidation / Q000187:drug effects; D008352:Mannich Bases / Q000737:chemistry*; D051379:Mice; D008862:Microsomes, Liver / Q000378:metabolism; D008968:Molecular Conformation; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C000588464:3-(((2,6-difluorophenyl)amino)methyl)-5-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)-1,3,4-oxadiazole-2(3H)-thione; C000588526:5-(2,3-dihydrobenzo(b)(1,4)dioxin-6-yl)-3-(((3,4,5-trifluorophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione; D000975:Antioxidants; D004146:Dioxanes; D008352:Mannich Bases; D010069:Oxadiazoles; C527681:1,4-benzodioxan
keywords: 1,3,4-Oxadiazole; 1,4-Benzodioxan; Antioxidant activity; Mannich base