An efficient method for the synthesis of guanidino prodrugs

A new class of guanidino prodrug is efficiently synthesized from an amine and an appropriate N,N'-bis(acyloxymethoxycarbonyl)-S-methylisothiourea. The N,N'-bis(acyloxymethoxycarbonyl)-S-methylisothiourea is readily prepared from S-methylisothiourea and the corresponding acyloxymethyl carbo...
Ausführliche Beschreibung

A new class of guanidino prodrug is efficiently synthesized from an amine and an appropriate N,N'-bis(acyloxymethoxycarbonyl)-S-methylisothiourea. The N,N'-bis(acyloxymethoxycarbonyl)-S-methylisothiourea is readily prepared from S-methylisothiourea and the corresponding acyloxymethyl carbonochloridate in good yield. The N,N'-bis(acyloxymethyl carbamate) derivatives of the highly basic guanidino group serve as lipophilic, uncharged, esterase-activatable prodrugs of simple guanidine containing molecules. Ausführliche Beschreibung