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Synthesis, biological evaluation and molecular modeling studies of novel 1,2,3-triazole-linked menadione-furan derivatives as P2X7 inhibitors. 2022

Juliana P S Dos Santos, and Ruan Carlos B Ribeiro, and Juliana V Faria, and Murilo L Bello, and Carolina G S Lima, and Fernanda P Pauli, and Amanda A Borges, and David R Rocha, and Matheus G Moraes, and Luana S M Forezi, and Vitor F Ferreira, and Robson X Faria, and Fernando de C da Silva
Laboratory of Studies in Experimental Pharmacology, Biomedical Science Institute, Universidade Federal Do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.

The P2X7 receptor (P2X7R) is an ion channel that promotes the passage of ions through the membrane through brief stimulation once activated by ATP, its endogenous opener. However, prolonged stimulation with ATP, which occurs in pathological processes, opens a nonselective pore in the plasma membrane, allowing the passage of large molecules and leading to cytokine release or even cell death. In this sense, the search for new inhibitors for this receptor has attracted a great deal of attention in recent years. Considering the booming of biomass upgrading reactions in recent years and the continued efforts to synthesize biologically active molecules containing the 1,2,3-triazole ring, in the present work, we aimed to investigate whether triazole-linked menadione-furan derivatives could present P2X7R inhibitory activity. The novel compounds were tested for their inhibitory activity on ATP-induced dye uptake in peritoneal macrophages. Some have shown promising results, having displayed IC50 values lower than that of the P2X7R inhibitor BBG. Molecular docking studies also indicated that the active compounds bind to an allosteric site on P2X7R, presenting potential P2X7R inhibition.

UI MeSH Term Description Entries
D005663 Furans Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran. Tetrahydrofurans
D000255 Adenosine Triphosphate An adenine nucleotide containing three phosphate groups esterified to the sugar moiety. In addition to its crucial roles in metabolism adenosine triphosphate is a neurotransmitter. ATP,Adenosine Triphosphate, Calcium Salt,Adenosine Triphosphate, Chromium Salt,Adenosine Triphosphate, Magnesium Salt,Adenosine Triphosphate, Manganese Salt,Adenylpyrophosphate,CaATP,CrATP,Manganese Adenosine Triphosphate,MgATP,MnATP,ATP-MgCl2,Adenosine Triphosphate, Chromium Ammonium Salt,Adenosine Triphosphate, Magnesium Chloride,Atriphos,Chromium Adenosine Triphosphate,Cr(H2O)4 ATP,Magnesium Adenosine Triphosphate,Striadyne,ATP MgCl2
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D058486 Receptors, Purinergic P2X7 A purinergic P2X neurotransmitter receptor that plays a role in pain sensation signaling and regulation of inflammatory processes. Purinergic P2X7 Receptor,P2X7 Purinoceptor,P2X7 Purinoceptors,P2X7 Receptor,P2Z Receptor,Purinergic Receptor P2X, Ligand-Gated Ion Channel, 7,Purinoceptor P2Z,P2X7 Receptor, Purinergic,P2X7 Receptors, Purinergic,P2Z, Purinoceptor,Purinergic P2X7 Receptors,Purinoceptor, P2X7,Purinoceptors, P2X7,Receptor, Purinergic P2X7
D058920 Purinergic P2X Receptor Antagonists Compounds that bind to and block the stimulation of PURINERGIC P2X RECEPTORS. Included under this heading are antagonists for specific P2X receptor subtypes. P2X Purinoceptor Antagonists,P2X1 Purinoceptor Antagonists,P2X2 Purinoceptor Antagonists,P2X3 Purinoceptor Antagonists,P2X4 Purinoceptor Antagonists,P2X5 Purinoceptor Antagonists,P2X6 Purinoceptor Antagonists,P2X7 Purinoceptor Antagonists,Purinergic P2X1 Receptor Antagonists,Purinergic P2X2 Receptor Antagonists,Purinergic P2X3 Receptor Antagonists,Purinergic P2X4 Receptor Antagonists,Purinergic P2X5 Receptor Antagonists,Purinergic P2X6 Receptor Antagonists,Purinergic P2X7 Receptor Antagonists,Antagonists, P2X Purinoceptor,Antagonists, P2X1 Purinoceptor,Antagonists, P2X2 Purinoceptor,Antagonists, P2X3 Purinoceptor,Antagonists, P2X4 Purinoceptor,Antagonists, P2X5 Purinoceptor,Antagonists, P2X6 Purinoceptor,Antagonists, P2X7 Purinoceptor,Purinoceptor Antagonists, P2X,Purinoceptor Antagonists, P2X1,Purinoceptor Antagonists, P2X2,Purinoceptor Antagonists, P2X3,Purinoceptor Antagonists, P2X4,Purinoceptor Antagonists, P2X5,Purinoceptor Antagonists, P2X6,Purinoceptor Antagonists, P2X7
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking
D024483 Vitamin K 3 A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. Menadione,2-Methyl-1,4-naphthalenedione,2-Methyl-1,4-naphthoquinone,2-Methylnaphthoquinone,Menadione Bisulfite,Menadione Sodium Bisulfite,Menadione Sodium Bisulfite, Trihydrate,Vicasol,Vikasol,Vitamin K3,Vitamin K3 Sodium Bisulfite,Bisulfite, Menadione,Bisulfite, Menadione Sodium,Sodium Bisulfite, Menadione

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