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WANG Fenghua, WANG Kai, SHEN Jianhua, CHEN Kaixian. Design, synthesis and antiproliferative activity of 3-hydroxy-4-quinolone compounds[J]. Journal of China Pharmaceutical University, 2014, 45(3): 286-292. DOI: 10.11665/j.issn.1000-5048.20140306
Citation: WANG Fenghua, WANG Kai, SHEN Jianhua, CHEN Kaixian. Design, synthesis and antiproliferative activity of 3-hydroxy-4-quinolone compounds[J]. Journal of China Pharmaceutical University, 2014, 45(3): 286-292. DOI: 10.11665/j.issn.1000-5048.20140306
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Design, synthesis and antiproliferative activity of 3-hydroxy-4-quinolone compounds

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  • A combination of the structural features of dihydromyricetin and quinolone antineoplastic compounds gave rise to 3-hydroxy-4-quinolone motif. Starting from 3, 5-dimethoxyaniline, the target compounds were prepared through a reaction cascade, including reductive amination, Friedel-Crafts reaction, microwave assisted ring closure, BBr3 catalyzed demethylation and Mannich reaction. Sixteen novel compounds were synthesized, and their structures were confirmed by IR, MS and 1H NMR. The antiproliferative activities of the compounds against A549 and NCI-H 460 cells were tested in MTT assay. Several compounds exhibited moderate antiproliferative activities against both cell lines, of which, compound 11b displayed the most robust inhibition towards NCI-H 460. Preliminary structural-activity relationships indicated that introduction of isopentenyl into the N-1 position of 3-hydroxy-4-quinolone motif would significantly improve the potency of the compounds.
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