Allobetulin derived seco-oleananedicarboxylates act as inhibitors of acetylcholinesterase

Lucie Heller; Stefan Schwarz; Anja Obernauer; René Csuk

doi:10.1016/j.bmcl.2015.04.086

Allobetulin derived seco-oleananedicarboxylates act as inhibitors of acetylcholinesterase

Bioorg Med Chem Lett. 2015 Jul 1;25(13):2654-6. doi: 10.1016/j.bmcl.2015.04.086. Epub 2015 May 5.

Authors

Lucie Heller¹, Stefan Schwarz¹, Anja Obernauer¹, René Csuk²

Affiliations

¹ Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
² Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany. Electronic address: rene.csuk@chemie.uni-halle.de.

PMID: 25980913
DOI: 10.1016/j.bmcl.2015.04.086

Abstract

Ring opening of allobetulone gave either seco-acid 8 or di-acid 4. These acids were converted into esters that were screened by Ellman's assay. A dibutenylester of low cytotoxicity (NIH 3T3 murine embryonic fibroblasts) was shown to be a good mixed-type inhibitor (Ki=3.39, Ki'=2.26μM) for acetylcholinesterase.

Keywords: Acetylcholinesterase inhibitor; Allobetulin; Alzheimer’s disease; Triterpene.

Publication types

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

MeSH terms

Acetylcholinesterase / metabolism
Alzheimer Disease / drug therapy
Animals
Cholinesterase Inhibitors / chemical synthesis
Cholinesterase Inhibitors / chemistry*
Cholinesterase Inhibitors / pharmacology*
Humans
Kinetics
Mice
NIH 3T3 Cells
Structure-Activity Relationship
Triterpenes / chemical synthesis
Triterpenes / chemistry*
Triterpenes / pharmacology*

Substances

Cholinesterase Inhibitors
Triterpenes
betulin
Acetylcholinesterase