The Synthesis of Bisguanidinoalkanes and Guanidinoalkanes, N- or N'-Substituted With Pyrimidines, as Analogues of Chlorhexidine

Abstract

A series of N,N???- alkanediylbis [N?-(5-halopyrimidin-2-yl)guanidine] salts has been synthesized along with N,N???-(trans-cyclohexane-1,4-diyl) bis [N'-(5-chloropyrimidin-2-yl)guanidine], N,N???-(cis-cyclohexane-1,4-diyl) bis [N?-(5-chloropyrimidin-2-yl)guanidine] dihydrochloride and N-(cis-4-amino-cyclohexan-1-yl)-N'-(5-chloropyrimidin-2-yl)guanidine dihydrochloride . Furthermore, a series of N-(alkan-1-yl)-N?-(5-chloropyrimidin-2yl)guanidine hydrochlorides and N-(6-aminohexan-1-yl)-N?-(5-chloropyrimidin-2-yl)guanidine dihydrochloride were synthesized. This series of compounds was prepared by displacement reactions of 2-methylsulfonylpyrimidines with bisguanidinoalkanes or by condensation of 5-chloro-2-cyanoaminopyrimidine (5-chloropyrimidin-2-ylcyanamide) with alkylamines .