Structure-based design and synthesis of HIV-1 protease inhibitors employing beta-D-mannopyranoside scaffolds

Paul V Murphy; Julie L O'Brien; Lorraine J Gorey-Feret; Amos B Smith 3rd

doi:10.1016/s0960-894x(02)00220-2

Structure-based design and synthesis of HIV-1 protease inhibitors employing beta-D-mannopyranoside scaffolds

Bioorg Med Chem Lett. 2002 Jul 8;12(13):1763-6. doi: 10.1016/s0960-894x(02)00220-2.

Authors

Paul V Murphy¹, Julie L O'Brien, Lorraine J Gorey-Feret, Amos B Smith 3rd

Affiliation

¹ Chemistry Department, Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland. paul.v.murphey@ucd.ie

PMID: 12067556
DOI: 10.1016/s0960-894x(02)00220-2

Abstract

A preliminary account on the structure-based design, synthesis and evaluation of peptidomimetic inhibitors of HIV-1 protease containing beta-D-mannopyranoside scaffolds is given. The compounds prepared had IC(50) values in the micromolar range. The results provide a platform for the development of more potent carbohydrate-based inhibitors of HIV-1 and other aspartic proteases.

Publication types

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

MeSH terms

Aspartic Acid Endopeptidases / chemistry
Binding Sites
Drug Design
HIV Protease Inhibitors / chemical synthesis*
HIV Protease Inhibitors / chemistry*
HIV Protease Inhibitors / pharmacology
HIV-1 / drug effects*
HIV-1 / enzymology
Inhibitory Concentration 50
Mannose / analogs & derivatives*
Mannose / chemical synthesis
Mannose / pharmacology
Molecular Conformation
Structure-Activity Relationship

Substances

HIV Protease Inhibitors
Aspartic Acid Endopeptidases
Mannose