Design of benzoic acid inhibitors of influenza neuraminidase containing a cyclic substitution for the N-acetyl grouping

W J Brouillette; V R Atigadda; M Luo; G M Air; Y S Babu; S Bantia

doi:10.1016/s0960-894x(99)00318-2

Design of benzoic acid inhibitors of influenza neuraminidase containing a cyclic substitution for the N-acetyl grouping

Bioorg Med Chem Lett. 1999 Jul 19;9(14):1901-6. doi: 10.1016/s0960-894x(99)00318-2.

Authors

W J Brouillette¹, V R Atigadda, M Luo, G M Air, Y S Babu, S Bantia

Affiliation

¹ Department of Chemistry, University of Alabama at Birmingham, 35294, USA.

PMID: 10450950
DOI: 10.1016/s0960-894x(99)00318-2

Abstract

A 2-pyrrolidinone ring containing a single hydroxymethyl side chain effectively replaces the N-acetylamino group of 4-(N-acetylamino)-3-guanidinobenzoic acid, a low micromolar inhibitor of influenza neuraminidase. This novel structural template affords new opportunities to evolve more potent benzoic acid inhibitors.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Benzoic Acid / chemistry*
Binding Sites
Computer Simulation
Drug Design
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / metabolism
Enzyme Inhibitors / pharmacology*
Hydrogen Bonding
Inhibitory Concentration 50
Models, Molecular
Neuraminidase / antagonists & inhibitors*
Neuraminidase / chemistry
Neuraminidase / metabolism
Orthomyxoviridae / enzymology*
Pyrrolidinones / chemistry
Pyrrolidinones / metabolism
Pyrrolidinones / pharmacology
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Pyrrolidinones
Benzoic Acid
Neuraminidase