Oxo- and thiooxo-imidazo[1,5-c]pyrimidine molecule library: beyond their interest in inhibition of Brucella suis histidinol dehydrogenase, a powerful protection tool in the synthesis of histidine analogues

Autor: Safia Ouahrani-Bettache, Jean-Yves Winum, Marie Lopez, François Turtaut, Stephan Köhler
Přispěvatelé: Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Centre d’études d’Agents Pathogènes et Biotechologies pour la Santé (CPBS), Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)
Rok vydání: 2014
Předmět:
Histidinol dehydrogenase
Pyrimidine
Stereochemistry
Brucella suis
Virulence Factors
Clinical Biochemistry
Pharmaceutical Science
Human pathogen
[CHIM.THER]Chemical Sciences/Medicinal Chemistry
010402 general chemistry
01 natural sciences
Biochemistry
Virulence factor
Brucellosis
Small Molecule Libraries
chemistry.chemical_compound
Structure-Activity Relationship
Oxo-imidazopyrimidines
Drug Discovery
[CHIM]Chemical Sciences
Humans
Histidine
Enzyme Inhibitors
Molecular Biology
chemistry.chemical_classification
biology
Molecular Structure
010405 organic chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Imidazoles
biology.organism_classification
0104 chemical sciences
Anti-Bacterial Agents
Alcohol Oxidoreductases
Enzyme
Pyrimidines
chemistry
Molecular Medicine
Bacteria
Anti-infectious agents
Zdroj: Bioorganic and Medicinal Chemistry Letters
Bioorganic and Medicinal Chemistry Letters, 2014, 24 (21), pp.5008-5010. ⟨10.1016/j.bmcl.2014.09.020⟩
Bioorganic and Medicinal Chemistry Letters, Elsevier, 2014, 24 (21), pp.5008-5010. ⟨10.1016/j.bmcl.2014.09.020⟩
ISSN: 1464-3405
0960-894X
DOI: 10.1016/j.bmcl.2014.09.020⟩
Popis: International audience; Histidinol dehydrogenase (HDH) has been established as a virulence factor for the human pathogen bacterium Brucella suis. Targeting such a virulence factor is a relevant anti-infectious approach as it could decrease the frequency of antibiotic resistance appearance. In this paper, we describe the synthesis of a family of oxo- and thioxo-imidazo[1,5-c]pyrimidines, potential enzyme inhibitors. Beyond their anti-HDH activity, the synthesis approach of these molecules, never described before, is highly original and these oxo- and thioxo- derivatives can improve dramatically the efficiency of the histidine protection pathway for the synthesis of histidine analogues.
Databáze: OpenAIRE
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