Synthesis and antitumor activities of novel CDDO-Me analogues

Yixue Qiao, Yi Mou, Zhangjian Huang, Yong Ai, Fenghua Kang, Yisheng Lai, Yihua Zhang

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)


The novel oleanolic acid derivatives 2a-2e were synthesized by introducing an α,β-unsaturated ketone moiety to C-ring of oleanolic acid (OA) via a nine-step reaction sequence, yielding an active CDDO-Me analogue (1), followed by coupling of C3-OH of 1 with various aliphatic and aromatic carboxylic acids, respectively. Derivatives 3a-3e were synthesized by substituting C-1 of compounds 2a-2e with bromine. The target compounds were characterized by IR, MS and 1H NMR spectra. All the target compounds showed strong inhibitory effects against two tumor cell lines (HepG2 and A549) to a varying extent. The anti-proliferative activities of active compounds 3b and 3c (IC50 =6.13 ±1.16 μmol/L and IC50 =5.49 ± 1.03 μmol/L, respectively) against HepG2 and A549 were more potent than compound 1 and comparable to the positive control CDDO-Me. In addition, all the target compounds displayed much weaker anti-proliferative activity against the two tumor cell lines than that against normal BEAS-2B cells. Compound 3c showed ten-fold selective inhibition against HepG2 relative to BEAS-2B cells, and is thus worthy of further study.

Original languageEnglish
Pages (from-to)289-293
Number of pages5
JournalJournal of China Pharmaceutical University
Issue number3
Publication statusPublished - 1 Jun 2015
Externally publishedYes


  • Antitumor activity
  • CDDO-Me
  • Oleanolic acid
  • Synthesis


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