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

Zewei Mao; Yan Li; Jingbo Chen; Yuanyuan Wang; Hongbin Zhang

doi:10.1016/j.bmcl.2010.05.075

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

Bioorg Med Chem Lett. 2010 Jul 15;20(14):4116-9. doi: 10.1016/j.bmcl.2010.05.075. Epub 2010 Jun 8.

Authors

Zewei Mao¹, Yan Li, Jingbo Chen, Yuanyuan Wang, Hongbin Zhang

Affiliation

¹ Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, PR China.

PMID: 20621726
DOI: 10.1016/j.bmcl.2010.05.075

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemistry*
Carbohydrate Conformation
Cell Line, Tumor
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / pharmacology*
Humans

Substances

Bridged Bicyclo Compounds
Diterpenes