Collect. Czech. Chem. Commun. 1995, 60, 894-902

Substituted 1-(2-Thienyl)cyclohexylamines and Related Compounds as Potential NMDA Antagonists

Karel Šindelář, Karel Dobrovský, Ivan Krejčí and Zdeněk Polívka

Research Institute for Pharmacy and Biochemistry,130 60 Prague 3, Czech Republic


Reactions of bisulfite addition compounds prepared in situ from cyclohexanone or 3,4,5,6-tetrahydro-2H-thiopyran-3-one with potassium cyanide and corresponding amines resulted with high yields in amino nitriles type of V and VI. These compounds were subjected to reactions with 2-thienylmagnesium bromide and in the case of the amino nitriles Vc and Vf with 5-bromo-2-thienylmagnesium bromide. Only in the case of compound Vf, a by-product X was isolated in addition to the desired 1-[1-(5-bromo-2-thienyl)-1-cyclohexyl]piperidine (VIIf). Compound VIIf was used for the synthesis of the carboxylic acid XI. The compounds prepared were tested by some methods of biochemical and behavioural pharmacology.