title: Design, synthesis, antifungal, and antioxidant activities of (E)-6-((2-phenylhydrazono)methyl)quinoxaline derivatives.
abstract: Different substituted phenylhydrazone groups were linked to the quinoxaline scaffold to provide 26 compounds (6a-6z). Their structures were confirmed by (1)H and (13)C NMR, MS, elemental analysis, and X-ray single-crystal diffraction. The antifungal activities of these compounds against Rhizoctonia solani were evaluated in vitro. Compound 6p is the most promising one among all the tested compounds with an EC50 of 0.16 μg·mL(-1), more potent than the coassayed positive control fungicide carbendazim (EC50: 1.42 μg·mL(-1)). In addition, these compounds were subjected to antioxidant assay by employing diphenylpicrylhydrazyl (DPPH) and mice microsome lipid peroxidation (LPO) methods. Most of these compounds are potent antioxidants. The strongest compounds are 6e (EC50: 7.60 μg·mL(-1), DPPH) and 6a (EC50: 0.96 μg·mL(-1), LPO), comparative to or more potent than the positive control Trolox [EC50: 5.90 μg·mL(-1) (DPPH) and 18.23 μg·mL(-1) (LPO)]. The structure and activity relationships were also discussed.
authors.affiliation: College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing Agricultural University , Nanjing 210095, People's Republic of China.
authors.forename: Mao
authors.initials: M
authors.lastname: Zhang
authors.forename: Zhi-Cheng
authors.initials: ZC
authors.lastname: Dai
authors.forename: Shao-Song
authors.initials: SS
authors.lastname: Qian
authors.forename: Jun-Yan
authors.initials: JY
authors.lastname: Liu
authors.forename: Yu
authors.initials: Y
authors.lastname: Xiao
authors.forename: Ai-Min
authors.initials: AM
authors.lastname: Lu
authors.forename: Hai-Liang
authors.initials: HL
authors.lastname: Zhu
authors.forename: Jian-Xin
authors.initials: JX
authors.lastname: Wang
authors.forename: Yong-Hao
authors.initials: YH
authors.lastname: Ye
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D004353:Drug Evaluation, Preclinical; D015227:Lipid Peroxidation; D008297:Male; D051379:Mice; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D008958:Models, Molecular; D011810:Quinoxalines / Q000737:chemistry*; D012232:Rhizoctonia / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: C000597880:(E)-6-((2-phenylhydrazono)methyl)quinoxaline; D000935:Antifungal Agents; D000975:Antioxidants; D011810:Quinoxalines
keywords: antioxidant; fungicide; phenylhydrazone; quinoxaline