Synthesis of 5-(4-alkylsulfanyl-[1, 2, 5]thiadiazol-3-yl)-3-methyl-1, 2, 3, 4-tetrahydropyrimidine oxalate salts and their evaluation as muscarinic receptor agonists.
The synthesis and biological test of 5-(4-alkylsulfanyl-[1, 2, 5]thiadiazol-3-yl)-3-me-thyl-1, 2, 3, 4-tetrahydropyrimidine oxalate salts 7 as muscarinic receptor agonists are described. The key intermediate 4 was obtained by a modified Strecker reaction and cyclization, and the 3-methyl-1, 2, 3, 4-tetrahydropyrimidines were obtained by subsequent substitution, quarternization, and reduction. The final products 7 were obtained as oxalic acid salts. The prepared compounds were examined in vitro for their binding affinities to the cloned human muscarinic receptor by the [(3)H]-NMS binding assay.
Jung
Myung Hee
MH
Korea Research Institute of Chemical Technology, PO Box 107, Yusong, Taejon 305-600, Korea. mhjung@krict.re.kr
Park
Jewn-Giew
JG
Park
Woo-Kyu
WK
D000818:Animals; D016466:CHO Cells; D003001:Cloning, Molecular; D006224:Cricetinae; D006801:Humans; D015394:Molecular Structure; D018721:Muscarinic Agonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010070:Oxalates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D043643:Receptor, Muscarinic M1; D011976:Receptors, Muscarinic / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D018721:Muscarinic Agonists; D010070:Oxalates; D011743:Pyrimidines; D043643:Receptor, Muscarinic M1; D011976:Receptors, Muscarinic; D013844:Thiazoles