Synthesis and antitumor activity of NO-donating CDDO analogues

Shi Bo Zhang, Zhen Zhen Zhang, Ye Ding, Yi Sheng Lai, Yi Mou, Yong Ai, Hui Ji, Yi Hua Zhang

Research output: Contribution to journalArticle

Abstract

The target compounds(4a-4k) were synthesized by building an α, β-unsaturated ketone moiety on C-ring of oleanolic acid (OA) via a five-step reaction sequence, yielding a CDDO analogue(1), followed by coupling of C3-OH in Compound 1 with substituted furoxans using butanedioic acid as a linker. The structures of the target compounds were identified by IR, MS and 1H NMR. The most active compound 4i displayed significant inhibitory effects (IC 50 =0.8-1.4 μmol/L) against the proliferation of four human tumor cell lines(HepG2, BEL-7402, MCF-7 and Caco-2), and was as potent as the positive control 2-cyano-3, 12-dioxooleana-1, 9(11)-dien-28-oic acid methyl ester(CDDO-Me). Compound 4i is thus worthy of further studies.

Original languageEnglish (US)
Pages (from-to)293-297
Number of pages5
JournalJournal of China Pharmaceutical University
Volume43
Issue number4
StatePublished - Aug 2012
Externally publishedYes

Fingerprint

Oleanolic Acid
Succinic Acid
Tumor Cell Line
Ketones
Esters
Acids
methyl 2-cyano-3,12-dioxoolean-1,9-dien-28-oate
furoxans
Proton Magnetic Resonance Spectroscopy

Keywords

  • Antitumor activity
  • CDDO
  • Furoxan
  • Nitric oxide donor
  • Oleanolic acid
  • Synthesis

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Pharmacology

Cite this

Zhang, S. B., Zhang, Z. Z., Ding, Y., Lai, Y. S., Mou, Y., Ai, Y., ... Zhang, Y. H. (2012). Synthesis and antitumor activity of NO-donating CDDO analogues. Journal of China Pharmaceutical University, 43(4), 293-297.

Synthesis and antitumor activity of NO-donating CDDO analogues. / Zhang, Shi Bo; Zhang, Zhen Zhen; Ding, Ye; Lai, Yi Sheng; Mou, Yi; Ai, Yong; Ji, Hui; Zhang, Yi Hua.

In: Journal of China Pharmaceutical University, Vol. 43, No. 4, 08.2012, p. 293-297.

Research output: Contribution to journalArticle

Zhang, SB, Zhang, ZZ, Ding, Y, Lai, YS, Mou, Y, Ai, Y, Ji, H & Zhang, YH 2012, 'Synthesis and antitumor activity of NO-donating CDDO analogues', Journal of China Pharmaceutical University, vol. 43, no. 4, pp. 293-297.
Zhang SB, Zhang ZZ, Ding Y, Lai YS, Mou Y, Ai Y et al. Synthesis and antitumor activity of NO-donating CDDO analogues. Journal of China Pharmaceutical University. 2012 Aug;43(4):293-297.
Zhang, Shi Bo ; Zhang, Zhen Zhen ; Ding, Ye ; Lai, Yi Sheng ; Mou, Yi ; Ai, Yong ; Ji, Hui ; Zhang, Yi Hua. / Synthesis and antitumor activity of NO-donating CDDO analogues. In: Journal of China Pharmaceutical University. 2012 ; Vol. 43, No. 4. pp. 293-297.
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AU - Ji, Hui

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