Coumarin inhibitors of gyrase B with N-propargyloxy-carbamate as an effective pyrrole bioisostere

Citation
Am. Periers et al., Coumarin inhibitors of gyrase B with N-propargyloxy-carbamate as an effective pyrrole bioisostere, BIOORG MED, 10(2), 2000, pp. 161-165
Citations number
22
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960-894X → ACNP
Volume
10
Issue
2
Year of publication
2000
Pages
161 - 165
Database
ISI
SICI code
0960-894X(20000117)10:2<161:CIOGBW>2.0.ZU;2-R
Abstract
The synthesis and biological profile in vitro of a series of coumarin inhib itors of gyrase B bearing a N-propargyloxy-carbamate at C-3' of noviose is presented. Replacement of the 5-methylpyrrole-2-carboxylate of coumarin dru gs with an N-propargyloxycarbamate bioisostere leads to analogues with impr oved antibacterial activity. Analysis of crystal structures of coumarin ant ibiotics with the 24 kDa N-terminal domain of the gyrase B protein provides a rational for the excellent inhibitory potency of C-3' N-alkoxycarbamates . (C) 2000 Elsevier Science Ltd. All rights reserved.