Citation: Meng Yanqiu, Xing Wen, Kuai Zhenyu, Zhang Weichen, Li Wei. Synthesis and Anti-Tumor Activities of Ring A Derived Analogues of Oleanolic Acid[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1417-1425. doi: 10.6023/cjoc201610033 shu

Synthesis and Anti-Tumor Activities of Ring A Derived Analogues of Oleanolic Acid

Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Corresponding author: Li Wei, myq@163.com
Received Date: 19 October 2016
Revised Date: 6 January 2017

Fund Project: the Excellent Talents in University of the Department of Education of Liaoning Province LR2013017the Scientific Research Project of the Shenyang Science and Technology Board F16-230-6-00the National Natural Science Foundation of China 21372156

Figures(5)

By means of computer aided drug design, simulation of apoptosis inhibiting protein complex glycine receptor kinase C-kit docking with active small molecules. Ten analogues were successfully synthesized by the introduction of nitrogen-containing heterocyclic compounds at ring A and the modification of the esterification and amidation at C(28) position in the natural product oleanolic acid. Their structures were charachterized by ¹H NMR, ¹³C NMR, MS and so forth. Their anti-tumor activities against KB, A549 cells in vitro were evaluated by methyl thiazolyl tetrazolium (MTT) assay. These results indicated that the objective of test compounds of two kinds of tumor cells have good inbitory activity, and 5', 6'-dihydro-olean-2-ene-[2, 3-b]pyrazin-12-ene-28-acyl-4"-monomethylaniline (Ⅰ₄) (IC₅₀＝2.67 μmol/L) and olean-2-ene-[2, 3-b]pyrimidine-12-ene-28-oic acid n-hextyl ester (Ⅱ₃) (IC₅₀＝1.03 μmol/L) have especially more potent inbitory activity on A549 tumor cells than 5-fluorouracil (IC₅₀＝7.39 μmol/L), which are worthy to be studied further.
- oleanolic acid analogues,
- synthesis,
- anti-tumor activity,
- molecular docking
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沈阳化工大学材料科学与工程学院沈阳 110142