Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation

Journal of Medicinal Chemistry
2021.0

Abstract

The ATP-gated P2X7 purinergic receptor (P2X7) is involved in the pathogenesis of many neurodegenerative diseases (NDDs). Several P2X7 antagonists have been developed, though none of them reached clinical trials for this indication. In this work, we designed and synthesized novel blood-brain barrier (BBB)-permeable derivatives as potential P2X7 antagonists. They comprise purine or xanthine cores linked to an aryl group through different short spacers. Compounds were tested in YO-PRO-1 uptake assays and intracellular calcium dynamics in a human P2X7-expressing HEK293 cell line, two-electrode voltage-clamp recordings in Xenopus laevis oocytes, and in interleukin 1β release assays in mouse peritoneal macrophages. BBB permeability was assessed by parallel artificial membrane permeability assays and P-glycoprotein ATPase activity. Dichloroarylpurinylethanones featured a certain P2X7 blockade, being compound 6 (2-(6-chloro-9H-purin-9-yl)-1-(2,4-dichlorophenyl)ethan-1-one), named ITH15004, the most potent, selective, and BBB-permeable antagonist. Compound 6 can be considered as a first non-nucleotide purine hit for future drug optimizations.

Knowledge Graph

Similar Paper

Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation
Journal of Medicinal Chemistry 2021.0
Pyroglutamide-Based P2X7 Receptor Antagonists Targeting Inflammatory Bowel Disease
Journal of Medicinal Chemistry 2020.0
Synthesis and structure-activity relationships of quinolinone and quinoline-based P2X7 receptor antagonists and their anti-sphere formation activities in glioblastoma cells
European Journal of Medicinal Chemistry 2018.0
Design and synthesis of adamantane-1-carbonyl thiourea derivatives as potent and selective inhibitors of h-P2X4 and h-P2X7 receptors: An Emerging therapeutic tool for treatment of inflammation and neurological disorders
European Journal of Medicinal Chemistry 2022.0
Therapeutic potentials and structure-activity relationship of 1,3-benzodioxole N-carbamothioyl carboxamide derivatives as selective and potent antagonists of P2X4 and P2X7 receptors
European Journal of Medicinal Chemistry 2022.0
The discovery and preclinical characterization of 6-chloro- N -(2-(4,4-difluoropiperidin-1-yl)-2-(2-(trifluoromethyl)pyrimidin-5-yl)ethyl)quinoline-5-carboxamide based P2X7 antagonists
Bioorganic & Medicinal Chemistry Letters 2016.0
N-Substituted Phenoxazine and Acridone Derivatives: Structure–Activity Relationships of Potent P2X4 Receptor Antagonists
Journal of Medicinal Chemistry 2012.0
1-Aryl-1 H - and 2-aryl-2 H -1,2,3-triazole derivatives blockade P2X7 receptor in vitro and inflammatory response in vivo
European Journal of Medicinal Chemistry 2017.0
Discovery and Structure Relationships of Salicylanilide Derivatives as Potent, Non-acidic P2X1 Receptor Antagonists
Journal of Medicinal Chemistry 2020.0
Potent Suppressive Effects of 1-Piperidinylimidazole Based Novel P2X7 Receptor Antagonists on Cancer Cell Migration and Invasion
Journal of Medicinal Chemistry 2016.0