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Int. J. Mol. Sci. 2016, 17(5), 653; doi:10.3390/ijms17050653

One-Pot Three-Component Synthesis of Novel Diethyl((2-oxo-1,2-dihydroquinolin-3-yl)(arylamino)methyl)phosphonate as Potential Anticancer Agents

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
College of Food and Biochemical Engineering, Gaungxi Science & Technology Normal University, Laibin 546199, China
Author to whom correspondence should be addressed.
Academic Editors: Ge Zhang, Aiping Lu and Hailong Zhu
Received: 29 March 2016 / Revised: 21 April 2016 / Accepted: 25 April 2016 / Published: 29 April 2016
(This article belongs to the Special Issue Translational Molecular Medicine & Molecular Drug Discovery)
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With the aim of discovering new anticancer agents, we have designed and synthesized novel α-aminophosphonate derivatives containing a 2-oxoquinoline structure using a convenient one-pot three-component method. The newly synthesized compounds were evaluated for antitumor activities against the A549 (human lung adenocarcinoma cell), HeLa (human cervical carcinoma cell), MCF-7 (human breast cancer cell), and U2OS (human osteosarcoma cell) cancer cell lines in vitro, employing a standard 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay. The results of pharmacological screening indicated that many compounds exhibited moderate to high levels of antitumor activities against the tested cancer cell lines and that most compounds showed more potent inhibitory activities comparable to 5-fluorouracil (5-FU) which was used as a positive control. The mechanism of representative compound 4u (diethyl((2-oxo-1,2-dihydroquinolin-3-yl)(phenyl-amino)methyl)phosphonate) indicated that the compound mainly arrested HeLa cells in S and G2 stages and was accompanied by apoptosis in HeLa cells. This action was confirmed by acridine orange/ethidium bromide staining, Hoechst 33342 staining, and flow cytometry. View Full-Text
Keywords: 2-oxoquinoline; α-aminophosphonate; one-pot method; anticancer activity; apoptosis 2-oxoquinoline; α-aminophosphonate; one-pot method; anticancer activity; apoptosis

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Fang, Y.-L.; Wu, Z.-L.; Xiao, M.-W.; Tang, Y.-T.; Li, K.-M.; Ye, J.; Xiang, J.-N.; Hu, A.-X. One-Pot Three-Component Synthesis of Novel Diethyl((2-oxo-1,2-dihydroquinolin-3-yl)(arylamino)methyl)phosphonate as Potential Anticancer Agents. Int. J. Mol. Sci. 2016, 17, 653.

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