AN EFFICIENT METHOD FOR THE SYNTHESIS OF GUANIDINO PRODRUGS

Authors
SAULNIER MG FRENNESSON DB DESHPANDE MS HANSEL SB VYAS DM
Citation
Mg. Saulnier et al., AN EFFICIENT METHOD FOR THE SYNTHESIS OF GUANIDINO PRODRUGS, Bioorganic & medicinal chemistry letters, 4(16), 1994, pp. 1985-1990
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
4
Issue
16
Year of publication
1994
Pages
1985 - 1990
Database
ISI
SICI code
0960-894X(1994)4:16<1985:AEMFTS>2.0.ZU;2-5
Abstract
A new class of guanidino prodrug is efficiently synthesized from an am ine and an appropriate '-bis(acyloxymethoxycarbonyl)-S-methylisothiour ea. The 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 containin g molecules.