Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives.

Abstract

A series of novel derivatives of 3-oxo-23-hydroxybetulinic acid was designed, synthesized, and evaluated for their antiproliferative activity against a panel of cancer cell lines (HL-60, BEL-7402, SF-763, HeLa, B16 and A375). The results indicated that majority of the derivatives exhibited more significant antitumor activity than the parent compound. In particular compound 10e showed the most potent activity with IC50 values of 5.85, 6.23 and 7.22 μM against B16, SF-763 and BEL-7402 cells, respectively. Furthermore, 10e inhibited tumor growth by 51.8% and 62.7% (w/w) in H22 and B16 xenograft mouse models, comparable to cyclophosphamide and 5-fluorouracil, respectively.

• Authors: Hengyuan Zhang, Peiqing Zhu, Jie Liu, Xue Yang, Shengtao Xu, Hequan Yao, Jieyun Jiang, Wencai Ye, Xiaoming Wu, Jinyi Xu
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 87 Pg. 159-67 (Nov 24 2014) ISSN: 1768-3254 [Electronic] France
• PMID: 25247772 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2014 Elsevier Masson SAS. All rights reserved.

Chemical References

• 3-oxo-23-hydroxybetulinic acid
• Antineoplastic Agents
• Triterpenes

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, pharmacology)
• Carcinoma, Hepatocellular (drug therapy, pathology)
• Cell Proliferation (drug effects)
• Humans
• Liver Neoplasms (drug therapy, pathology)
• Melanoma, Experimental (drug therapy, pathology)
• Mice
• Molecular Structure
• Neoplasms (drug therapy, pathology)
• Structure-Activity Relationship
• Triterpenes (chemistry)
• Tumor Cells, Cultured
• Xenograft Model Antitumor Assays