Synthesis, <i>In-Vitro</i> Activity and Metabolic Properties of Quinocetone and Structurally Similar Compounds
| Author | Keyu Zhang | en |
| Author | Chunmei Wang | en |
| Author | Xiaoyang Wang | en |
| Author | Haihong Zheng | en |
| Author | Juan Zhao | en |
| Author | Mi Wang | en |
| Author | Sui Xiao | en |
| Author | Chenzhong Fei | en |
| Author | Wenli Zheng | en |
| Author | Lifang Zhang | en |
| Author | Feiqun Xue | en |
| Issued Date | 2017-04-30 | en |
| 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. | en |
| DOI | https://doi.org/10.22037/ijpr.2017.2039 | en |
| Keyword | Quinocetone | en |
| Keyword | 2-Propenyl moiety | en |
| Keyword | Cytotoxicity mechanism | en |
| Keyword | Toxiccophore | en |
| Publisher | Brieflands | en |
| Title | Synthesis, <i>In-Vitro</i> Activity and Metabolic Properties of Quinocetone and Structurally Similar Compounds | en |
| Type | Original Article | en |
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