Amino(oxo)acetate moiety: A new functional group to improve the cytotoxicity of betulin derived carbamates

Lucie Heller; Vincent Perl; Jana Wiemann; Ahmed Al-Harrasi; René Csuk

doi:10.1016/j.bmcl.2016.04.055

Amino(oxo)acetate moiety: A new functional group to improve the cytotoxicity of betulin derived carbamates

Bioorg Med Chem Lett. 2016 Jun 15;26(12):2852-2854. doi: 10.1016/j.bmcl.2016.04.055. Epub 2016 Apr 20.

Authors

Lucie Heller¹, Vincent Perl¹, Jana Wiemann¹, Ahmed Al-Harrasi², René Csuk¹

Affiliations

¹ Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
² University of Nizwa, Chair of Oman's Medicinal Plants and Marine Natural Products, PO Box 33, Birkat Al-Mauz, Nizwa, Oman.

PMID: 27142753
DOI: 10.1016/j.bmcl.2016.04.055

Abstract

While 3-O-acetylated betulin derivatives carrying a carbamate moiety at position C-28 are of rather low cytotoxicity for human tumor cell lines, the corresponding C-3 amino(oxo) acetates show good cytotoxicity. For example, an EC50 as low as 2.0μM was found for (3β) 28-{[(hexylamino)carbonyl]oxy}lup-20(29)-en-3-yl amino(oxo)acetate (16) employing the ovarian cancer cell line A2780.

Keywords: Betulin; Cytotoxicity; Triterpene.

Publication types

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

MeSH terms

Acetates / chemistry
Acetates / pharmacology*
Carbamates / chemistry
Carbamates / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Dose-Response Relationship, Drug
Humans
Molecular Structure
Structure-Activity Relationship
Triterpenes / chemical synthesis
Triterpenes / chemistry
Triterpenes / pharmacology*

Substances

Acetates
Carbamates
Triterpenes
betulin