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Research Paper

Development of terphenyl-2-methyloxazol-5(4H)-one derivatives as selective reversible MAGL inhibitors

ORCID Icon, , , , , , , ORCID Icon & ORCID Icon show all
Pages 1240-1252 | Received 28 Jul 2017, Accepted 23 Aug 2017, Published online: 22 Sep 2017

References

  • Di Marzo V, Petrosino S. Endocannabinoids and the regulation of their levels in health and disease. Curr Opin Lipidol 2007;18:129–40.
  • Labar G, Wouters J, Lambert DM. A review on the monoacylglycerol lipase: at the interface between fat and endocannabinoid signalling. Curr Med Chem 2010;17:2588–607.
  • Mulvihill MM, Nomura DK. Therapeutic potential of monoacylglycerol lipase inhibitors. Life Sci 2013;92:492–7.
  • Nomura DK, Morrison BE, Blankman JL, et al. Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation. Science 2011;334:809–13.
  • Kinsey SG, O’Neal ST, Long JZ, et al. Inhibition of endocannabinoid catabolic enzymes elicits anxiolytic-like effects in the marble burying assay. Pharmacol Biochem Behav 2011;98:21–7.
  • Ramesh D, Ross GR, Schlosburg JE, et al. Blockade of endocannabinoid hydrolytic enzymes attenuates precipitated opioid withdrawal symptoms in mice. J Pharmacol Exp Ther 2011;339:173–85.
  • Kopp F, Komatsu T, Nomura DK, et al. The glycerophospho metabolome and its influence on amino acid homeostasis revealed by brain metabolomics of GDE1(-/-) mice. Chem Biol 2010;17:831–40.
  • Muccioli GG, Labar G, Lambert DM. CAY10499, a novel monoglyceride lipase inhibitor evidenced by an expeditious MGL assay. Chembiochem 2008;9:2704–10.
  • Zvonok N, Pandarinathan L, Williams J, et al. Covalent inhibitors of human monoacylglycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis. Chem Biol 2008;15:854–62.
  • King AR, Lodola A, Carmi C, et al. A critical cysteine residue in monoacylglycerol lipase is targeted by a new class of isothiazolinone-based enzyme inhibitors. Br J Pharmacol 2009;157:974–83.
  • Long JZ, Li W, Booker L, et al. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol 2009;5:37–44.
  • Matuszak N, Muccioli GG, Labar G, Lambert DM. Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors. J Med Chem 2009;52:7410–20.
  • Kapanda CN, Masquelier J, Labar G, et al. Synthesis and pharmacological evaluation of 2,4-dinitroaryldithiocarbamate derivatives as novel monoacylglycerol lipase inhibitors. J Med Chem 2012;55:5774–83.
  • Schlosburg JE, Blankman JL, Long JZ, et al. Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nat Neurosci 2010;13:1113–19.
  • Hernandez-Torres G, Cipriano M, Heden E, et al. A reversible and selective inhibitor of monoacylglycerol lipase ameliorates multiple sclerosis. Angew Chem Int Ed Engl 2014;53:13765–70.
  • Tuccinardi T, Granchi C, Rizzolio F, et al. Identification and characterization of a new reversible MAGL inhibitor. Bioorg Med Chem 2014;22:3285–91.
  • Granchi C, Rizzolio F, Palazzolo S, et al. Structural optimization of 4-chlorobenzoylpiperidine derivatives for the development of potent, reversible, and selective monoacylglycerol lipase (MAGL) inhibitors. J Med Chem 2016;59:10299–314.
  • Granchi C, Rizzolio F, Bordoni V, et al. 4-Aryliden-2-methyloxazol-5(4H)-one as a new scaffold for selective reversible MAGL inhibitors. J Enzyme Inhib Med Chem 2016;31:137–46.
  • Poli G, Giuntini N, Martinelli A, Tuccinardi T. Application of a FLAP-consensus docking mixed strategy for the identification of new fatty acid amide hydrolase inhibitors. J Chem Inf Model 2015;55:667–75.
  • Maestro, version 9.0. Portland (OR): Schrödinger Inc; 2009. Available from: https://www.schrodinger.com/
  • Macromodel, version 9.7. Portland (OR): Schrödinger Inc; 2009. Available from: https://www.schrodinger.com/
  • Poli G, Martinelli A, Tuccinardi T. Reliability analysis and optimization of the consensus docking approach for the development of virtual screening studies. J Enzym Inhib Med Ch 2016;31:167–73.
  • Bertrand T, Auge F, Houtmann J, et al. Structural basis for human monoglyceride lipase inhibition. J Mol Biol 2010;396:663–73.
  • Mileni M, Kamtekar S, Wood DC, et al. Crystal structure of fatty acid amide hydrolase bound to the carbamate inhibitor URB597: discovery of a deacylating water molecule and insight into enzyme inactivation. J Mol Biol 2010;400:743–54.
  • Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model 1999;17:57–61.
  • Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.
  • DOCK, version 6.5. San Francisco (CA): Molecular Design Institute, University of California; 1998. Available from: http://dock.compbio.ucsf.edu/
  • QUACPAC, version 1.5.0. Santa Fe (NM): OpenEye Scientific Software, Inc.; 2013. Available from: https://www.eyesopen.com/
  • FRED, version 3.0.0. Santa Fe (NM): OpenEye Scientific Software, Inc.; 2013. Available from: https://www.eyesopen.com/
  • OMEGA, version 2.4.6. Santa Fe (NM): OpenEye Scientific Software, Inc.; 2013. Available from: https://www.eyesopen.com/
  • Hawkins PC, Skillman AG, Warren GL, et al. Conformer generation with OMEGA: algorithm and validation using high quality structures from the Protein Databank and Cambridge Structural Database. J Chem Inf Model 2010;50:572–84.
  • Hawkins PC, Nicholls A. Conformer generation with OMEGA: learning from the data set and the analysis of failures. J Chem Inf Model 2012;52:2919–36.
  • Tuccinardi T, Poli G, Dell’Agnello M, et al. Receptor-based virtual screening evaluation for the identification of estrogen receptor beta ligands. J Enzym Inhib Med Ch 2015;30:662–70.
  • Glide, version 5.0. Portland (OR): Schrödinger Inc; 2009.
  • Verdonk ML, Cole JC, Hartshorn MJ, et al. Improved protein-ligand docking using GOLD. Proteins 2003;52:609–23.
  • Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010;31:455–61.
  • Korb O, Monecke P, Hessler G, et al. pharmACOphore: multiple flexible ligand alignment based on ant colony optimization. J Chem Inf Model 2010;50:1669–81.
  • Case DA, Berryman JT, Betz RM, et al. AMBER, version 14. San Francisco (CA): University of California; 2015.
  • York DM, Darden TA, Pedersen LG. The effect of long-range electrostatic interactions in simulations of macromolecular crystals - a comparison of the ewald and truncated list methods. J Chem Phys 1993;99:8345–8.
  • Leadbeater NE, Marco M. Ligand-free palladium catalysis of the Suzuki reaction in water using microwave heating. Org Lett 2002;4:2973–6.
  • Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem Rev 1995;95:2457–83.
  • Littke AF, Fu GC. A convenient and general method for Pd-catalyzed Suzuki cross-couplings of aryl chlorides and arylboronic acids. Angew Chem Int Edit 1998;37:3387–8.
  • Long JZ, Nomura DK, Vann RE, et al. Dual blockade of FAAH and MAGL identifies behavioral processes regulated by endocannabinoid crosstalk in vivo. Proc Natl Acad Sci USA 2009;106:20270–5.
  • Chang JW, Niphakis MJ, Lum KM, et al. Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates. Chem Biol 2012;19:579–88.
  • Wang X, Sarris K, Kage K, et al. Synthesis and evaluation of benzothiazole-based analogues as novel, potent, and selective fatty acid amide hydrolase inhibitors. J Med Chem 2009;52:170–80.
  • Tuccinardi T, Poli G, Romboli V, et al. Extensive consensus docking evaluation for ligand pose prediction and virtual screening studies. J Chem Inf Model 2014;54:2980–6.
  • Kuhn B, Kollman PA. Binding of a diverse set of ligands to avidin and streptavidin: an accurate quantitative prediction of their relative affinities by a combination of molecular mechanics and continuum solvent models. J Med Chem 2000;43:3786–91.
  • Tuccinardi T, Manetti F, Schenone S, et al. Construction and validation of a RET TK catalytic domain by homology modeling. J Chem Inf Model 2007;47:644–55.
  • Tuccinardi T, Granchi C, Iegre J, et al. Oxime-based inhibitors of glucose transporter 1 displaying antiproliferative effects in cancer cells. Bioorg Med Chem Lett 2013;23:6923–7.
  • Petrou A, Geronikaki A, Terzi E, et al. Inhibition of carbonic anhydrase isoforms I, II, IX and XII with secondary sulfonamides incorporating benzothiazole scaffolds. J Enzym Inhib Med Ch 2016;31:1306–11.