Design and synthesis of 2,6-disubstituted-8-amino imidazo[1,2a]pyridines, a promising privileged structure

Autor: Nicolas Renault, Raphaël Bolteau, Laurence Agouridas, Romain Duroux, Rajaa Boulahjar, Angela Rincon Arias, Amélie Barczyk, Patricia Melnyk, Saïd Yous, Mathilde Coevoet
Přispěvatelé: Centre de Recherche Jean-Pierre AUBERT Neurosciences et Cancer - U1172 Inserm - U837 (JPArc), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Lille Nord de France (COMUE)-Université de Lille, Lille Inflammation Research International Center - U 995 (LIRIC), Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Centre de Recherche Jean-Pierre AUBERT Neurosciences et Cancer - U837 (JPArc), Université Lille Nord de France (COMUE)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille, Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille), Melnyk, Patricia
Jazyk: angličtina
Rok vydání: 2018
Předmět:
0301 basic medicine
Receptor
Adenosine A2A
Pyridines
[CHIM.THER] Chemical Sciences/Medicinal Chemistry
Clinical Biochemistry
Pharmaceutical Science
[CHIM.THER]Chemical Sciences/Medicinal Chemistry
Biochemistry
Coupling reaction
Catalysis
A2A receptor
privileged structure
palladium-catalyzed coupling reaction
03 medical and health sciences
Structure-Activity Relationship
0302 clinical medicine
Suzuki reaction
Cell Line
Tumor
Drug Discovery
Humans
Molecular Biology
Cell Proliferation
Binding Sites
Chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
[CHIM.ORGA] Chemical Sciences/Organic chemistry
amino-imidazopyridine
Combinatorial chemistry
3. Good health
Adenosine A2 Receptor Antagonists
Protein Structure
Tertiary
Molecular Docking Simulation
030104 developmental biology
Adenosine Receptor A2a
HEK293 Cells
Drug Design
Molecular Medicine
Amine gas treating
030217 neurology & neurosurgery
Palladium
Zdroj: Bioorganic and Medicinal Chemistry
Bioorganic and Medicinal Chemistry, Elsevier, 2018, 26 (12), pp.3296-3307. ⟨10.1016/j.bmc.2018.04.057⟩
Bioorganic and Medicinal Chemistry, 2018, 26 (12), pp.3296-3307. ⟨10.1016/j.bmc.2018.04.057⟩
ISSN: 0968-0896
1464-3391
DOI: 10.1016/j.bmc.2018.04.057⟩
Popis: International audience; Imidazo[1,2a]pyridines have gained much interest in the field of medicinal chemistry research. In the aim of accessing new privileged structure, we decided to design and synthesize 8-aminated-imidazo[1,2a]pyridines substituted on positions 2 and 6. This scaffold, rarely found in the literature, was obtained via palladium-catalyzed coupling reactions (Suzuki reaction or N-hydroxysuccinimidyl activated ester method) and tested on adenosine receptor A2A. We demonstrated how incorporation of an exocyclic amine enhanced affinity towards this receptor while maintaining low cytotoxicity.
Databáze: OpenAIRE
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