Synthesis and anticancer activity of novel oleanolic acid derivatives

Ye Ding, Zhen Zhen Zhang, Zhang Jian Huang, Yi Mou, Hui Ji, Yi Sheng Lai, Yi Hua Zhang

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

Starting from oleanolic acid (OA), the target compounds (10a-10i) were synthesized via introducting α,β-unsaturated ketone moiety to OA by 7-step successive reactions including benzylation, acetylation, oxidization, bromine substitution-elimination, etc., followed by coupling of C28-carboxyl with substituted furoxans via a glycine linker. All the target compounds were identified by IR, MS and 1H NMR. MTT assay results showed that compounds 10a-10i displayed much stronger inhibitory effects than OA on the proliferation of four human tumor cell lines. The anti-proliferative activity of 10a-10e and 10i against human hepatoma HepG2 cell was comparable to that of the positive control 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester (CDDO-Me).

Original languageEnglish (US)
Pages (from-to)385-391
Number of pages7
JournalJournal of China Pharmaceutical University
Volume42
Issue number5
StatePublished - Oct 1 2011

Keywords

  • Anticancer activity
  • Furoxan
  • NO donor
  • Oleanolic acid
  • α,β-unsaturated ketone

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Fingerprint Dive into the research topics of 'Synthesis and anticancer activity of novel oleanolic acid derivatives'. Together they form a unique fingerprint.

  • Cite this

    Ding, Y., Zhang, Z. Z., Huang, Z. J., Mou, Y., Ji, H., Lai, Y. S., & Zhang, Y. H. (2011). Synthesis and anticancer activity of novel oleanolic acid derivatives. Journal of China Pharmaceutical University, 42(5), 385-391.