Recombination of diterpenoid structure units: synthesis of antitumor amides bearing functionalized bicyclo[3.2.1]octane ring.

Abstract

In this work, 23 new amides (14-36) bearing a representative diterpenoid structure unit, the functionalized bicyclo[3.2.1]octane ring, have been synthesized and its antitumor potential is studied. In vitro studies demonstrate that a number of amides with the bicyclo[3.2.1]oct-3-en-2-one subunit are active against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 tumor cell lines. The hybrid derivative, compound 20, was found to be the most potent compound (IC(50)=1.05 microM against HL-60) and more active than cisplatin (DDP), the positive control. Additionally, compound 20 exhibited broad spectrum in vitro anticancer activity with IC(50) values of 1.1-4.3 microM against the five tested cancer cell lines.

• Authors: Zewei Mao, Yan Li, Jingbo Chen, Yuanyuan Wang, Hongbin Zhang
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 20 Issue 14 Pg. 4116-9 (Jul 15 2010) ISSN: 1464-3405 [Electronic] England
• PMID: 20621726 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: 2010 Elsevier Ltd. All rights reserved.

Chemical References

• Bridged Bicyclo Compounds
• Diterpenes

Topics

• Bridged Bicyclo Compounds (chemistry)
• Carbohydrate Conformation
• Cell Line, Tumor
• Diterpenes (chemical synthesis, chemistry, pharmacology)
• Humans