A prodrug system for hydroxylamines based on esterase catalysis

Ana Conejo-Garcia; Christopher J Schofield

doi:10.1016/j.bmcl.2005.06.026

A prodrug system for hydroxylamines based on esterase catalysis

Bioorg Med Chem Lett. 2005 Sep 15;15(18):4004-9. doi: 10.1016/j.bmcl.2005.06.026.

Authors

Ana Conejo-Garcia¹, Christopher J Schofield

Affiliation

¹ Department of Chemistry and Oxford Centre for Molecular Sciences, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.

PMID: 15990293
DOI: 10.1016/j.bmcl.2005.06.026

Abstract

The synthesis and reactivity of hydroxy hydroxamates as models for a prodrug form of hydroxylamine are described. Gamma-hydroxy hydroxamates were found to enable hydroxylamine release via lactonisation. Hydroxamates were found to undergo esterase catalysed hydrolysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Esterases / metabolism*
Hydrolysis
Hydroxylamines / chemistry*
Hydroxylamines / metabolism*
Hydroxylation
Lactones / chemistry
Lactones / metabolism
Magnetic Resonance Spectroscopy
Molecular Structure
Prodrugs / chemical synthesis*
Prodrugs / chemistry
Prodrugs / metabolism*
Structure-Activity Relationship

Substances

Hydroxylamines
Lactones
Prodrugs
Esterases