Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

被引:33
作者
Phutdhawong, Weerachai [1 ]
Chuenchid, Apiwat [2 ]
Taechowisan, Thongchai [3 ]
Sirirak, Jitnapa [2 ]
Phutdhawong, Waya S. [2 ]
机构
[1] Kasetsart Univ, Fac Liberal Arts & Sci, Dept Sci, Kamphaeng Sean Campus, Kamphaeng Saen 73140, Nakhon Pathom, Thailand
[2] Silpakorn Univ, Fac Sci, Dept Chem, Mueang Nakhon Pathom 73000, Nakhon Pathom, Thailand
[3] Silpakorn Univ, Fac Sci, Dept Microbiol, Mueang Nakhon Pathom 73000, Nakhon Pathom, Thailand
关键词
coumarin3-carboxamides; coumarins; pyranocoumarins; anticancer activity; antibacterial activity;
D O I
10.3390/molecules26061653
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of novel coumarin-3-carboxamide derivatives were designed and synthesized to evaluate their biological activities. The compounds showed little to no activity against gram-positive and gram-negative bacteria but specifically showed potential to inhibit the growth of cancer cells. In particular, among the tested compounds, 4-fluoro and 2,5-difluoro benzamide derivatives (14b and 14e, respectively) were found to be the most potent derivatives against HepG2 cancer cell lines (IC50 = 2.62-4.85 mu M) and HeLa cancer cell lines (IC50 = 0.39-0.75 mu M). The activities of these two compounds were comparable to that of the positive control doxorubicin; especially, 4-flurobenzamide derivative (14b) exhibited low cytotoxic activity against LLC-MK2 normal cell lines, with IC50 more than 100 mu M. The molecular docking study of the synthesized compounds revealed the binding to the active site of the CK2 enzyme, indicating that the presence of the benzamide functionality is an important feature for anticancer activity.
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页数:12
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