1,737
Views
9
CrossRef citations to date
0
Altmetric
Research Paper

Design, synthesis and evaluation of 2-aryl benzoxazoles as promising hit for the A2A receptor

, , , , , , & show all
Pages 850-864 | Received 24 Mar 2017, Accepted 18 May 2017, Published online: 29 Jun 2017

References

  • Fargo K, Bleiler L. Alzheimer’s disease facts and figures. Alzheimers Dement 2014;10:47–92.
  • Panza F, Solfrizzi V, Barulli MR, et al. Coffee, tea, and caffeine consumption and prevention of late-life cognitive decline and dementia: a systematic review. J Nutr Health Aging 2015;19:313–28.
  • Solfrizzi V, Panza F, Imbimbo BP, et al. Coffee consumption habits and the risk of mild cognitive impairment: the Italian longitudinal study on aging. J Alzheimers Dis 2015;47:889–99.
  • Flaten V, Laurent C, Coelho JE, et al. From epidemiology to pathophysiology: what about caffeine in Alzheimer’s disease? Biochem Soc Trans 2014;42:587–92.
  • Xu K, Di Luca DG, Orrú M, et al. Neuroprotection by caffeine in the MPTP model of Parkinson’s disease and its dependence on adenosine A2A receptors. Neuroscience 2016;322:129–37.
  • Dall’Igna OP, Fett P, Gomes MW, et al. Caffeine and adenosine A(2a) receptor antagonists prevent beta-amyloid (25-35)-induced cognitive deficits in mice. Exp Neurol 2007;203:241–5.
  • Preti D, Baraldi PG, Moorman AR, et al. History and perspectives of A2A adenosine receptor antagonists as potential therapeutic agents. Med Res Rev 2015;35:790–848.
  • Shook BC, Jackson PF. Adenosine A(2A) receptor antagonists and Parkinson’s disease. ACS Chem Neurosci 2011;2:555–67.
  • Hauser RA, Olanow CW, Kieburtz KD, et al. Tozadenant (SYN115) in patients with Parkinson’s disease who have motor fluctuations on levodopa: a phase 2b, double-blind, randomised trial. Lancet Neurol 2014;13:767–76.
  • Pinna A. Adenosine A2A receptor antagonists in Parkinson’s disease: progress in clinical trials from the newly approved istradefylline to drugs in early development and those already discontinued. CNS Drugs 2014;28:455–74.
  • Kondo T, Mizuno Y, Japanese Istradefylline Study Group. A long-term study of istradefylline safety and efficacy in patients with Parkinson disease. Clin Neuropharmacol 2015;38:41–6.
  • Laurent C, Burnouf S, Ferry B, et al. A2A adenosine receptor deletion is protective in a mouse model of Tauopathy. Mol Psychiatry 2016;21:97–107.
  • de Lera Ruiz M, Lim YH, Zheng J. Adenosine A2A receptor as a drug discovery target. J Med Chem 2014;57:3623–50.
  • Müller CE, Ferré S. Blocking striatal adenosine A2A receptors: a new strategy for basal ganglia disorders. Recent Pat CNS Drug Discov 2007;2:1–21.
  • Robinson SJ, Petzer JP, Terre’Blanche G, et al. 2-Aminopyrimidines as dual adenosine A1/A2A antagonists. Eur J Med Chem 2015;104:177–88.
  • Tokuyama H, Okano K, Fujiwara H, et al. Total synthesis of dictyodendrins A-E. Chem Asian J 2011;6:560–72.
  • Jones G, Willett P, Glen RC. Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J Mol Biol 1995;245:43–53.
  • Lopes LV, Cunha RA, Ribeiro JA. Cross talk between A1 and A2A adenosine receptors in the hippocampus and cortex of young adult and old rats. J Neurophysiol 1999;82:3196–203.
  • Townsend-Nicholson A, Schofield PR. A threonine residue in the seventh transmembrane domain of the human A1 adenosine receptor mediates specific agonist binding. J Biol Chem 1994;269:2373–6.
  • Stehle JH, Rivkees SC, Lee JJ, et al. Molecular cloning and expression of the cDNA for a novel A2-adenosine receptor subtype. Mol Endocrinol 1992;6:384–93.
  • Salvatore CA, Jacobson MA, Taylor HE, et al. Molecular cloning and characterization of the human A3 adenosine receptor. Proc Natl Acad Sci U S A 1993;90:10365–9.
  • Lipinski CA, Lombardo F, Dominy BW, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;46:3–26.
  • Sangster J. Wiley series in solution chemistry. Volume 2. Chichester: John Wiley and Sons; 1997.
  • Banker MJ, Clark TH, Williams JA. Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding. J Pharm Sci 2003;92:967.
  • Hidalgo IJ, Raub TJ, Borchardt RT. Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 1989;96:736–49.
  • Obach RS, Baxter JG, Liston TE, et al. The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data. J Pharmacol Exp Ther 1997;283:46–58.
  • Jaakola VP, Griffith MT, Hanson MA, et al. The 2.6 angstrom crystal structure of a human A2A adenosine receptor bound to an antagonist. Science 2008;322:1211–17.
  • Liu W, Chun E, Thompson AA, et al. Structural basis for allosteric regulation of GPCRs by sodium ions. Science 2012;337:232–6.
  • Congreve M, Andrews SP, Doré AS, et al. Discovery of 1,2,4-triazine derivatives as adenosine A(2A) antagonists using structure based drug design. J Med Chem 2012;55:1898–903.
  • Sabbadin D, Ciancetta A, Moro S. Perturbation of fluid dynamics properties of water molecules during G protein-coupled receptor-ligand recognition: the human A2A adenosine receptor as a key study. J Chem Inf Model 2014;54:2846–55.
  • Lenselink EB, Beuming T, Sherman W, et al. Selecting an optimal number of binding site waters to improve virtual screening enrichments against the adenosine A2A receptor. J Chem Inf Model 2014;54:1737–46.
  • Keränen H, Gutiérrez-de-Terán H, Åqvist J. Structural and energetic effects of A2A adenosine receptor mutations on agonist and antagonist binding. PLoS One 2014;9:e108492.
  • Yuan S, Hu Z, Filipek S, et al. W246(6.48) opens a gate for a continuous intrinsic water pathway during activation of the adenosine A2A receptor. Angew Chem Int Ed Engl 2015;54:556–9.
  • Venkatakrishnan AJ, Deupi X, Lebon G, et al. Molecular signatures of G-protein-coupled receptors. Nature 2013;494:185–94.
  • Wisastra R, Ghizzoni M, Boltjes A, et al. Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases. Bioorg Med Chem 2012;20:5027–32.
  • Wen X, Bakali JE, Deprez-Poulain R, et al. Efficient propylphosphonic anhydride (®T3P) mediated synthesis of benzothiazoles, benzoxazoles and benzimidazoles. Tetrahedron Lett 2012;53:2440–3.
  • Evaluation and Licensing Division, Pharmaceutical and Food Safety Bureau Ministry of Health. Labour and Welfare [Online] 2015. Available from: https://www.pmda.go.jp/files/000153870.pdf/
  • Müller CE. Prodrug approaches for enhancing the bioavailability of drugs with low solubility. Chem Biodivers 2009;6:2071–83.
  • Slee DH, Zhang X, Moorjani M, et al. Identification of novel, water-soluble, 2-amino-N-pyrimidin-4-yl acetamides as A2A receptor antagonists with in vivo efficacy. J Med Chem 2008;51:400–6.
  • Mikkelsen GK, Langgård M, Schroder TJ, et al. Synthesis and SAR studies of analogues of 4-(3,3-dimethyl-butyrylamino)-3,5-difluoro-N-thiazol-2-yl-benzamide (Lu AA41063) as adenosine A2A receptor ligands with improved aqueous solubility. Bioorg Med Chem Lett 2015;25:1212–16.
  • Zheng J, Yang Z, Li X, et al. Optimization of 6-heterocyclic-2-(1H-pyrazol-1-yl)-N-(pyridin-2-yl)pyrimidin-4-amine as potent adenosine A2A receptor antagonists for the treatment of Parkinson’s disease. ACS Chem Neurosci 2014;5:674–82.