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- Title
Synthesis, In-Vitro Activity and Metabolic Properties of Quinocetone and Structurally Similar Compounds.
- Authors
Keyu Zhang; Chunmei Wang; Xiaoyang Wang; Haihong Zheng; Juan Zhao; Mi Wang; Sui Xiao; Chenzhong Fei; Wenli Zheng; Lifang Zhang; Feiqun Xue
- Abstract
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.
- Subjects
QUINOXALINES; NITROANILINE; AROMATIC compounds; AROMATIC aldehydes; CHEMICAL structure
- Publication
Iranian Journal of Pharmaceutical Research, 2017, Vol 16, Issue 2, p1
- ISSN
1735-0328
- Publication type
Article