Synthesis of 5-(n-isopropylthiocarbamoyl)-spinaceamines: Analogs of antisecretory and antiulcer derivatives of spinaceamine

A series of 5-(N-isopropylthiocarbamoyl) derivatives of spinaceamine and spinacine have been synthesized for pharmacological testing. N-Phenacylium salts were obtained via the interaction of 1-and 1,2-substituted imidazo4,5-c]pyridines with p-methoxyphenacyl bromide. The reduction of N-phenacylium salts with sodium borohydride in alcohol leads to the formation of 5-(β-hydroxy-β-p-methoxyphenetyl)spinaceamines, and subsequent boiling with concentrated hydrochloric acid leads to cleavage of the terminal C-N⁵ bonds with the formation of 1-substituted and 1,2-disubstituted spinaceamines. Final treatment with isopropylisothiocyanate converts these intermediate compounds into the target 5-(N-isopropylthiocarbamoyl) derivatives. Lithium and potassium salts of spinacine were reacted with isopropylisothiocyanate to obtain the corresponding thioureas, which were converted into hydrochlorides by treatment with hydrogen chloride saturated ether. __________ Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 2, pp. 5–9, February, 2006.