Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

Authors

Kwankamol Sastraruji, University of WollongongFollow
Thanapat Sastraruji, University of WollongongFollow
Alison T. Ung, University of Technology, SydneyFollow
Renate Griffith, University of New South Wales
Araya Jatisatienr, Chiang Mai University
Stephen G. Pyne, University of WollongongFollow

RIS ID

59474

Publication Details

Sastraruji, K., Sastraruji, T., Ung, A. T., Griffith, R., Jatisatienr, A. & Pyne, S. G. (2012). Synthesis of stemofoline analogues as acetylcholinesterase inhibitors. Tetrahedron, 68 (35), 7103-7115.

Abstract

Thirty two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine.

Grant Number

ARC/DP0879491

Additional Grant Number

http://purl.org/au-research/grants/ARC/DP0879491