Synthesis of Tetrahydropyridinyltriazolothiadiazines as Possible Muscarinic Agonists  

作　　者：GuoQiangHU WenLongHUANG HaiWANG 

机构地区：[1]MedicalCollegeofHenanUnversity.Kaifeng475001 [2]ChinaPharmaceuticalUniversity,Nanjing210009 [3]AcademyofMilitaryMedicalSciences,Beijing100850

出　　处：《Chinese Chemical Letters》2005年第1期1-3,共3页中国化学快报（英文版）

基　　金：supported by the State Basic Research and Development Project(No.G1998051112);the Science Foundation of Henan University(XK02041)

摘　　要：Amino-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol 1 were condensed with 2-bromo-1- (substituted phenyl)ethanone to give pyridinyltriazolothiadiazines 2a^c, which were quaternarized with methyl iodide and oxidized with 30 % hydrogen peroxide to afford the corresponding methyl pyridinium salts 3a^c and pyridine-1-oxides 4a^c, respectively. The reduction of compounds 3 and 4 with NaBH4 in methanol produced the target compounds 1-methyl-1, 2, 5, 6-tetrahydropyridin-3- yl)-6-aryl-s-triazolothiadiazines 5a^c and 3-(1-hydroxyl-1, 2, 5, 6-tetrahydropyridin -3-yl)-6-aryl- s-triazolothiadiazines 6a^c, respectively. The endothelium vascular relaxing activity of the target compounds was screened.Amino-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol 1 were condensed with 2-bromo-1- (substituted phenyl)ethanone to give pyridinyltriazolothiadiazines 2a^c, which were quaternarized with methyl iodide and oxidized with 30 % hydrogen peroxide to afford the corresponding methyl pyridinium salts 3a^c and pyridine-1-oxides 4a^c, respectively. The reduction of compounds 3 and 4 with NaBH4 in methanol produced the target compounds 1-methyl-1, 2, 5, 6-tetrahydropyridin-3- yl)-6-aryl-s-triazolothiadiazines 5a^c and 3-(1-hydroxyl-1, 2, 5, 6-tetrahydropyridin -3-yl)-6-aryl- s-triazolothiadiazines 6a^c, respectively. The endothelium vascular relaxing activity of the target compounds was screened.

关 键 词：TETRAHYDROPYRIDINE triazolothiadiazine muscarinic agonist vascular activity. 

分 类 号：R971.7[医药卫生—药品] R914.5[医药卫生—药学]