Synthesis of 5-(4-alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4-tetrahydropyrimidi ne oxalate salts and their evaluation as muscarinic receptor agonists.
The synthesis and biological testing of 5-(4-alkoxy-[1,2,5]thiadiazol-3-yl)-3-methyl-1,2,3,4-tetrahydro pyrimidine oxalate salts 8 as muscarinic receptor agonists are described. The key intermediate 4 was obtained by modified Strecker reaction and cyclization of starting material 1. Subsequent alkoxy substitution, quaternization, and reduction afforded 7. For the sake of purity and stability of the final products 8, the 3-methyl-1,2,3,4-tetrahydropyrimidines were obtained as oxalic acid salts. All final compounds were examined in vitro for their binding affinities to the cloned human muscarinic receptor by the [3H]-NMS binding assay.
Park
J G
JG
Korea Research Institute of Chemical Technology, Yusong, Taejon, Korea.
Lee
M J
MJ
Kong
J Y
JY
Jung
M H
MH
D000544:Alzheimer Disease / Q000188:drug therapy; D001667:Binding, Competitive; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018721:Muscarinic Agonists / Q000138:chemical synthesis* / Q000494:pharmacology; D019832:N-Methylscopolamine / Q000378:metabolism; D011485:Protein Binding; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D043643:Receptor, Muscarinic M1; D011976:Receptors, Muscarinic / Q000378:metabolism; D011994:Recombinant Proteins / Q000378:metabolism; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D018721:Muscarinic Agonists; D011743:Pyrimidines; D043643:Receptor, Muscarinic M1; D011976:Receptors, Muscarinic; D011994:Recombinant Proteins; D013830:Thiadiazoles; D019832:N-Methylscopolamine