- Convenient synthesis of quinocetone metabolites: Characterization, theoretical investigation, and cytotoxicity study
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Quinocetone (3-methyl-2-quinoxalinbenzenevinylketo-1,4-dioxide; QCT) is a new promising antimicrobial growth promoter for quinoxalines. The identification of the major metabolites of QCT has resulted in a number of studies regarding its metabolic pathway.
- Zhang, Jiaheng,Li, Linxia,Li, Yubo,Peng, Bing,Li, Songqing,Zhou, Zhiqiang,Gao, Haixiang,Zhang, Suxia
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- Synthesis of the possible metabolites of quinocetone in animals
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The possible metabolites of quinocetone in animals had been prepared with different selective reagent by three synthetic routes. It was their principal reaction that Na2S2O4 reduced quinoxaline-1,4-dioxide derivatives to quinoxaline derivatives, H 2O2 s oxidized 2-carboxyl-quinoxaline derivatives to 2-carboxyl-quinoxaline-1 -oxide ones and P(OCH3) 3 reduced 2-carboxyl- quinoxaline-1,4-dioxide derivatives to 3-carboxyl-quinoxaline-1-oxide ones. The title compounds ware confirmed with NMR,UV, FAB-MS, et al.
- Li, Jian-Yong,Zhang, Ji-Yu,Zhou, Xu-Zheng,Li, Jin-Shan,Lu, Run-Hua
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- Improved synthesis of quinocetone and its two deoxy metabolites
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Oxidation of o-nitroaniline with sodium hypochlorite afforded benzofurazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetylacetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline--1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinox-aline-1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium acetate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one in 88.5 and 92 % yield, respectively. Furthermore, the synthesized quinocetone, and its deoxy derivatives were characterized by1H-NMR,13C-NMR and elemental analysis.
- Li, Yuwen,Qiu, Mei,Bai, Yubin,Qu, Shaoqi,Hao, Zhihui
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p. 265 - 270
(2018/04/12)
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- REACTIONS OF 2-ACETYL-3-METHYLQUINOXALINE 1,4-DIOXIDE AND ITS DERIVATIVES
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2-Cinnamoyl-3-methylquinoxaline 1,4-dioxide (2) was inert to hydrochloric acid in refluxing ethanol.When a xylene solution of 2-acetyl-3-methylquinoxaline 1,4-dioxide (1-dioxide) was refluxed overnight, the dioxide was reduced mainly to 1,4-oxide and the oxidative products from xylene were also obtained. 2-Cinnamoyl-3-methylquinoxaline 4-oxide (4a) and 3-methyl-4-oxido-2-quinoxalyl 4-phenyl-1,3-butadienyl ketone (4b) were quantitatively cyclized into 4-methyl-3-oxo-1-phenyl- and 4-methyl-3-oxo-1-styryl-3H-pyrroloquinoxalin-10-ium chloride (6a and 6 b), respectively , when the ethanolic solution were refluxed in the presence of hydrochloric acid.
- Matoba, Katsuhide,Terada, Takashi,Sugiura, Masaru
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