Combinatorial synthesis of SSAO inhibitors using sonogashira coupling: SAR of aryl propargylic amines

C Conn; R Shimmon; F Cordaro; T L Hargraves; P Ibrahim

doi:10.1016/s0960-894x(01)00506-6

Combinatorial synthesis of SSAO inhibitors using sonogashira coupling: SAR of aryl propargylic amines

Bioorg Med Chem Lett. 2001 Oct 8;11(19):2565-8. doi: 10.1016/s0960-894x(01)00506-6.

Authors

C Conn¹, R Shimmon, F Cordaro, T L Hargraves, P Ibrahim

Affiliation

¹ Department of Chemistry, Materials and Forensic Sciences, University of Technology, Sydney, PO Box 123, Broadway, NSW 2007, Australia. c.conn@uts.edu.au

PMID: 11551750
DOI: 10.1016/s0960-894x(01)00506-6

Abstract

The structure-activity relationships for semicarbazide-sensitive amine oxidase (SSAO) inhibitors based on arylpropynylamines was investigated using solution-phase combinatorial Sonogashira coupling. The results suggest that binding to the active site occurs by coordination of the amine to the proximal copper(II) and formation of a pi-complex between topaquinone and the electron-rich aryl group of the inhibitor.

MeSH terms

Amine Oxidase (Copper-Containing) / antagonists & inhibitors*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Molecular Conformation
Pargyline / analogs & derivatives*
Pargyline / chemical synthesis
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Pargyline
Amine Oxidase (Copper-Containing)