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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 6: 1417 - 1425

DOI: https://doi.org/10.6023/cjoc201610033

Articles

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

  • Meng Yanqiu ,
  • Xing Wen ,
  • Kuai Zhenyu ,
  • Zhang Weichen ,
  • Li Wei
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  • Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Received date: 2016-10-19

  Revised date: 2017-01-06

  Online published: 2017-02-20

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372156), the Excellent Talents in University of the Department of Education of Liaoning Province (No. LR2013017), and the Scientific Research Project of the Shenyang Science and Technology Board (No.F16-230-6-00).

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Abstract

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.

Key words： oleanolic acid analogues; synthesis; anti-tumor activity; molecular docking

Cite this article

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

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