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Synthesis and Muscarinic Activity of 1,2,3,4‐Tetrahydropyrimidine Derivatives
Author(s) -
Jung Myung Hee,
Park JewnGiew,
Yang Kong Jae,
Lee MiJeoung
Publication year - 2001
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/1521-4184(200103)334:3<79::aid-ardp79>3.0.co;2-7
Subject(s) - muscarinic acetylcholine receptor , chemistry , stereochemistry , pharmacology , biochemistry , medicine , receptor
Abstract 3‐Methyl‐1,2,3,4‐tetrahydropyrimidine‐5‐carbaldehyde O ‐substituted oximes 4 and 1‐(3‐methyl‐1,2,3,4‐tetrahydropyrimidin‐5‐yl)ethanone O ‐substituted oximes 9 have been prepared as bioisosteric congeners of arecoline which is a muscarinic agonist for treatment of Alzheimer s disease. Starting from pyrimidine‐5‐carbaldehyde 1 , formation of the 3‐methylpyrimidinium salt and subsequent reduction afforded 1,2,3,4‐tetrahydropyrimidine derivatives which were converted into oxalate salts in the interest of purity and stability. Binding affinities of prepared compounds for the cloned human muscarinic M 1 receptor (h‐M 1 ) were determined by radioligand binding assay using [ 3 H]‐N‐methylscopolamine (NMS).