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Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one

1
School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation (Yantai University), Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai 264005, China
2
Department of Biochemistry and Molecular Medicine, School of Medicine, University of California Davis, Sacramento, CA 95817, USA
*
Author to whom correspondence should be addressed.
Received: 9 January 2019 / Revised: 25 February 2019 / Accepted: 26 February 2019 / Published: 3 March 2019
(This article belongs to the Section Medicinal Chemistry)
3,4-dihydropyrimidin-2(1H)-one compounds (DHPMs) possess extensive biological activities and are mainly prepared via Biginelli reaction and N-alkylation. In the present study, selective alkylation of N1 was investigated by using tetrabutylammonium hydroxide. In vitro cytotoxicity study on all synthesized compounds demonstrated that introduction of the aryl chain in the R3 as well as the low electron-donating group in the R1 of DHPMs contributed to the anti-proliferative potency. A larger value of the partition coefficient (Log P) and suitable polar surface area (PSA) values were both found to be important in order to maintain the antitumor activity. The results from in vivo study indicated the great potential of compound 3d to serve as a lead compound for novel anti-tumor drugs to treat glioma. Pharmacophore study regarding the structure-activity relations of DHPMs were also conducted. Our results here could provide a guide for the design of novel bioactive 3,4-dihydropyrimidin-2(1H)-one compounds. View Full-Text
Keywords: 3,4-dihydropyrimidin-2(1H)-ones; N1-alkylation; structure-activity relationship; in vivo experiments; anticancer activities 3,4-dihydropyrimidin-2(1H)-ones; N1-alkylation; structure-activity relationship; in vivo experiments; anticancer activities
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MDPI and ACS Style

Liu, Y.; Liu, J.; Zhang, R.; Guo, Y.; Wang, H.; Meng, Q.; Sun, Y.; Liu, Z. Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one. Molecules 2019, 24, 891. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24050891

AMA Style

Liu Y, Liu J, Zhang R, Guo Y, Wang H, Meng Q, Sun Y, Liu Z. Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one. Molecules. 2019; 24(5):891. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24050891

Chicago/Turabian Style

Liu, Ye, Jiaqi Liu, Renmei Zhang, Yan Guo, Hongbo Wang, Qingguo Meng, Yuan Sun, and Zongliang Liu. 2019. "Synthesis, Characterization, and Anticancer Activities Evaluation of Compounds Derived from 3,4-Dihydropyrimidin-2(1H)-one" Molecules 24, no. 5: 891. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24050891

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