Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones

Ali Koohang; Nathan D Majewski; Erika L Szotek; Aye Aye Mar; David A Eiznhamer; Michael T Flavin; Ze-Qi Xu

doi:10.1016/j.bmcl.2009.02.107

Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones

Bioorg Med Chem Lett. 2009 Apr 15;19(8):2168-71. doi: 10.1016/j.bmcl.2009.02.107. Epub 2009 Mar 3.

Authors

Ali Koohang¹, Nathan D Majewski, Erika L Szotek, Aye Aye Mar, David A Eiznhamer, Michael T Flavin, Ze-Qi Xu

Affiliation

¹ Advanced Life Sciences, Inc, Research and Development, Woodridge, IL 60517, USA.

PMID: 19286375
DOI: 10.1016/j.bmcl.2009.02.107

Abstract

New A-ring modified betulin and dihydrobetulin derivatives possessing the 2-cyano-1-en-3-one moiety were prepared and tested for cytotoxicity in seven cancer cell lines. The most active agent 9a synthesized in this account was further demonstrated to induce apoptosis and to activate caspases in malignant melanoma cells.

Publication types

Comparative Study

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis
Antineoplastic Agents, Phytogenic / toxicity
Apoptosis / drug effects
Betulinic Acid
Cell Line, Tumor
Cell Proliferation / drug effects
Growth Inhibitors / chemical synthesis*
Growth Inhibitors / toxicity*
Humans
Pentacyclic Triterpenes
Triterpenes / chemical synthesis*
Triterpenes / toxicity*

Substances

Antineoplastic Agents, Phytogenic
Growth Inhibitors
Pentacyclic Triterpenes
Triterpenes
Betulinic Acid