Combinatorial synthesis of SSAO inhibitors using sonogashira coupling: SAR of aryl propargylic amines.
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.
Conn
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Department of Chemistry, Materials and Forensic Sciences, University of Technology, Sydney, PO Box 123, Broadway, NSW 2007, Australia. c.conn@uts.edu.au
Shimmon
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Cordaro
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Hargraves
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Ibrahim
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D006631:Amine Oxidase (Copper-Containing) / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008968:Molecular Conformation; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D010293:Pargyline; D006631:Amine Oxidase (Copper-Containing)