ACYLOXYMETHYL AS A DRUG PROTECTING GROUP - SYNTHESIS AND REACTIVITY OF N-ACYLOXYMETHYLSULFONAMIDE PRODRUGS

Authors
CALHEIROS T ILEY J LOPES F MOREIRA R
Citation
T. Calheiros et al., ACYLOXYMETHYL AS A DRUG PROTECTING GROUP - SYNTHESIS AND REACTIVITY OF N-ACYLOXYMETHYLSULFONAMIDE PRODRUGS, Bioorganic & medicinal chemistry letters, 5(9), 1995, pp. 937-940
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
5
Issue
9
Year of publication
1995
Pages
937 - 940
Database
ISI
SICI code
0960-894X(1995)5:9<937:AAADPG>2.0.ZU;2-R
Abstract
Tertiary N-acyloxymethylsulfonamide prodrugs 3, encompassing penicilli n and sulfonamide antibiotics, have been synthesised. The pH-independe nt hydrolysis of these compounds ocurrs via the rate-determining forma tion of an N-sulfonyl iminium ion. SCF-MO calculations using the PM3 m ethod indicate that iminium ion formation is slightly favoured, when c ompared with the corresponding amides, by ca. 10 kJmol(-1).