Synthesis, In-Vitro Activity and Metabolic Properties of Quinocetone and Structurally Similar Compounds

文献类型： 外文期刊

第一作者： Zhang, Keyu

作者： Zhang, Keyu;Wang, Chunmei;Wang, Xiaoyang;Zheng, Haihong;Zhao, Juan;Wang, Mi;Xiao, Sui;Fei, Chenzhong;Zheng, Wenli;Zhang, Lifang;Xue, Feiqun

作者机构：

关键词： quinocetone;2-propenyl moiety;cytotoxicity mechanism;toxiccophore

期刊名称：IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH （ 影响因子：1.696； 五年影响因子：1.998 ）

ISSN： 1735-0328

年卷期： 2017 年 16 卷 2 期

页码：

收录情况： SCI

摘要： To investigate the cytotoxicity mechanism of quinocetone from the perspective of chemical structure, quinocetone and other new quinoxaline-1, 4-dioxide derivatives were synthesized, and evaluated for their activities, and analysed for the metabolic characteristics. Quinocetone and other new quinoxaline-1,4-dioxide derivatives were synthesized, and evaluated for their activities, and analysed for the metabolic characteristics. The synthetic route started from 2-nitroaniline which was reacted with 3-bromopropanoic acid followed by the reaction of acetylacetone to afford 2-acetyl-3-methylquinoxaline-1, 4-dioxide. The aldol condensation of the later compound with aromatic aldehydes led to the formation of the quinocetone structure similar compounds. A number of prepared derivatives exerted antimicrobial activities and cytotoxicity potency. Analysis of metabolic pathways in vitro displayed 2-propenyl and N -> O groups were the major sites. The results suggested 2-propenyl group exert important role in cytotoxicity of quinocetone and is another major toxiccophore for quinocetone, and different electronic substituents in arylidene aryl ring could affect the electronic arrangement of 2-propenyl and N -> O groups to chang the cytostatic potency.

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