Halogenated 2-amino-4H-pyrano[3,2-h]quinoline-3-carbonitriles as antitumor agents and structure–activity relationships of the 4-, 6-, and 9-positions

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• 作者：Ahmed M. Fouda
• 关键词：8 ; Hydroxyquinoline derivatives ; 4H ; Pyrano[3 ; 2 ; h]quinoline ; Antitumor ; Lipophilicity ; SAR
• 刊名：Medicinal Chemistry Research
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：26
• 期：2
• 页码：302-313
• 全文大小：
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120
• 卷排序：26

文摘

A series of halogenated 2-amino-4-aryl-4H-pyrano[3,2-h]quinoline-3-carbonitrile derivatives were prepared via interaction of 8-hydroxyquinoline, 5-chloro-8-hydroxyquinoline, and 8-hydroxy-2-methylquinoline with various α-cyanocinnamonitriles. The assignments of the structure of all synthesized compounds were based on spectral data. The cytotoxic activities of the synthesized compounds against four human tumor cell lines MCF-7, HCT-116, HepG-2, and A549 in comparison with the reference drugs Vinblastine and Colchicine were determined by microculture tetrazolium assay. Several compounds showed significant cytotoxic activity. The structure–activity relationship studies reported that the substitution at 4-, 6-, and 9-positions in several 2-amino-4H-pyrano[3,2-h]quinoline nucleus with the specific halogen atom and lipophilicity increases the ability of the molecule against the different cell lines.