An Efficient Method for the Synthesis of Guanidino Prodrugs.
2010
Abstract 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.
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