Synthesis and Biological Evaluation of Oxygen-containing Heterocyclic Ring-fused 23-Hydroxybetulinic Acid Derivatives as Antitumor Agents

Hengyuan Zhang, Fangzheng Li, Peiqing Zhu, Jie Liu, Hequan Yao, Jieyun Jiang, Wencai Ye, Xiaoming Wu, Jinyi Xu

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A collection of isoxazole and oxadiazole substituted 23-hydroxybetulinic acid (HBA) derivatives were designed, synthesized and evaluated for their antitumor activity. Most of the newly synthesized compounds exhibited more potent antiproliferative activity than patent compound 23-hydroxybetulinic acid, especially 13e and 14a were about four- to sevenfold more potent against all tested cancer cell lines than 23-hydroxybetulinic acid. Furthermore, the in vivo antitumor activity of 13e and 14a was validated in H22 liver cancer and B16 melanoma xenograft mouse models. The structure-activity relationships of these 23-hydroxybetulinic acid derivatives were also discussed based on the present investigation.

Original languageEnglish
Pages (from-to)424-431
Number of pages8
JournalChemical Biology and Drug Design
Volume86
Issue number4
DOIs
StatePublished - Oct 1 2015

Keywords

  • 23-hydroxybetulinic acid
  • antiproliferative activity
  • antitumor activity
  • heterocycle
  • isoxazole
  • oxadiazole

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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