Synthesis of trifluoromethyl-substituted mono-carbonyl curcumin analogs and evaluation of their anti-proliferation activity on lung cancer cells
10.13220/j.cnki.jipr.2018.08.006
- VernacularTitle:三氟甲基取代单羰基姜黄素的合成及其对肺癌细胞的抗增殖活性
- Author:
Jie YANG
1
;
Yong-Jing ZHAO
;
Xiao-Jing LI
;
Su-Su MENG
;
Hua-Lei ZHANG
;
Guo-Yun LIU
Author Information
1. 聊城大学药学院
- Keywords:
curcumin analog;
trifluoromethyl;
lung cancer;
anti-proliferation;
synthesis
- From:
Journal of International Pharmaceutical Research
2018;45(8):593-596
- CountryChina
- Language:Chinese
-
Abstract:
Objective To synthesize trifluoromethyl-substituted mono-carbonyl curcumin analogs and investigate their effects on the proliferation of human lung cancer cells A549 and NCI-H460. Methods Six mono-carbonyl curcumin analogs 1a-1f were synthesized via Aldol condensation using commercially available 2-trifluoromethyl benzadehyde and different ketones (actone, cyclopentanone, cyclohexanone, piperid-4-one, and 1-methylpiperid-4-one). MTT method was used to test the effect of 1a-1f on the proliferation of A549 and NCI-H460 cells. Results Compared with curcumin, most of the mono-carbonyl curcumin analogs 1a-1f exhibited anti-proliferation activity on the A549 cells. The values of IC50 were lower than that of curcumin (P＜0.01), and 1a and 1f showed much better activities both on the A549 and NCI-H460 cells, with their IC50 values were much lower than that of curcumin (P＜0.01).Among them, 1f showed better medicinal chemical properties, with the relative molecular mass less than 500, cLogP 5.25, and the polar surface area (PSA) 37.38, which was more better accorded with the Lipinski′s five rules. Conclusion Six mono-carbonyl curcumin analogs 1a-1f were synthesized, and 1f showed much better anti-proliferation activity on A549 and NCI-H460 cells.
