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Research Article

Synthesis of 3,4-dihydro-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxides and their evaluation as ligands for NMDA receptor glycine binding site

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Pages 664-673 | Received 02 Apr 2015, Accepted 09 Apr 2015, Published online: 26 Jun 2015

References

  • Watkins JC, Collingridge GL, eds. The NMDA receptor. 2nd ed. England: Oxford University Press; 1994:522
  • Traynelis SF, Wollmuth LP, McBain CJ, et al. Glutamate receptor ion channels: structure, regulation, and function. Pharmacol Rev 2010;62:405–96
  • Lipton SA, Rosenberg PA. Excitatory amino acids as a final common pathway for neurologic disorders. N Engl J Med 1994;330:613–22
  • Danysz W, Parsons CG. Glycine and N-methyl-d-aspartate receptors: physiological significance and possible therapeutic applications. Pharmacol Rev 1998;50:597–664
  • Johnson JW, Ascher P. Glycine potentiates the NMDA response in cultured mouse brain neurons. Nature 1987;325:529–31
  • Jansen M, Dannhardt G. Antagonists and agonists at the glycine site of the NMDA receptor for therapeutic interventions. Eur J Med Chem 2003;38:661–70
  • Catarzi D, Colotta V, Varano F. Competitive Gly/NMDA receptor antagonists. Curr Top Med Chem 2006;6:809–21
  • Nagata R, Katayama S, Ohtani K, Tanaka H, Shimago K. Tricyclic quinoxalinediones, aza-kynurenic acids, and indole-2-carboxylic acids as in vivo active NMDA-glycine antagonists. Curr Top Med Chem 2006;6:733–45
  • Leeson PD, Iversen LL. The glycine site on the NMDA receptor: structure–activity relationships and therapeutic potential. J Med Chem 1994;37:4053–67
  • Danysz W, Kozela E, Parsons CG, et al. Peripherally acting NMDA receptor/glycineB site receptor antagonists inhibit morphine tolerance. Neuropharmacology 2005;48:360–71
  • Deur C, Agrawal AK, Baum H, et al. N-(6,7-dichloro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-N-alkylsulfonamides as peripherally restricted N-methyl-d-aspartate receptor antagonists for the treatment of pain. Bioorg Med Chem Lett 2007;17:4599–603
  • Henrich M, Bauer A, Nagel J, et al. Glycine B antagonists. PCT Patent Appl WO 2010;139481 (09.12.2010)
  • Leeson PD, Baker R, Carling RW, et al. Kynurenic acid derivatives. Structure–activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-d-aspartate receptor. J Med Chem 1991;34:1243–52
  • Jimonet P, Audiau F, Aloup JC, et al. Synthesis and SAR of 2H-1,2,4-benzothiadiazine-1,1-dioxide-3-carboxylic acid derivatives as novel potent glycine antagonists of the NMDA receptor-channel complex. Bioorg Med Chem Lett 1994;4:2735–40
  • Colotta V, Catarzi D, Varano F, et al. Synthesis and biological evaluation of a series of quinazoline-2-carboxylic acids and quinazoline-2,4-diones as glycine-NMDA antagonists: a pharmacophore model based approach. Arch Pharm (Weinheim) 1997;330:129–34
  • Varano F, Catarzi D, Colotta V, et al. Synthesis of 2-substituted-6,8-dichloro-3,4-dihydro-3-oxo-2H-1,4-benzothiazine-1,1-dioxides and -1-oxides as glycine-NMDA receptor antagonists. Farmaco 1998;53:752–7
  • Costa BM, Irvine MW, Fang G, et al. Structure–activity relationships for allosteric NMDA receptor inhibitors based on 2-naphthoic acid. Neuropharmacology 2012;62:1730–6
  • Foster AC, Wong EH. The novel anticonvulsant MK-801 binds to the activated state of the N-methyl-d-aspartate receptor in the rat brain. Br J Pharmacol 1987;91:403–9
  • Parsons CG, Danysz W, Quack G, et al. Novel systemically active antagonists of the glycine site of the N-methyl-d-aspartate receptor: electrophysiological, biochemical and behavioral characterization. J Pharmacol Exp Ther 1997;283:1264–75
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the folin phenol reagent. J Biol Chem 1951;193:265–75
  • Hartree EF. Determination of protein: a modification of the Lowry method that gives a linear photometric response. Anal Biochem 1972;48:422–7
  • Vidal A, Madelmont JC, Mounetou EA. Simple and efficient synthesis of methyl 3,4-dihydro-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide from saccharin sodium salt. Synthesis 2006;4:591–3
  • Wells GJ, Tao M, Josef KA, Bihovsky R. 1,2-Benzothiazine 1,1-dioxide P2–P3 peptide mimetic aldehyde calpain I inhibitors. J Med Chem 2001;44:3488–503
  • Xu L, Shu H, Liu Y, Zhang S, Trudell ML. Oxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives. Tetrahedron 2006;62:7902–10
  • Baron BM, Siegel BW, Harrison BL, Gross RS, Hawes C, Towers P. [3H]MDL 105,519, a high-affinity radioligand for the N-methyl-d-aspartate receptor-associated glycine recognition site. J Pharmacol Exp Ther 1996;279:62–8
  • Baron BM, Harrison BL, Kehne JH, et al. Pharmacological characterization of MDL 105,519, an NMDA receptor glycine site antagonist. Eur J Pharmacol 1997;323:181–92
  • Höfner G, Wanner K-Th. Characterization of the binding [3H]MDL 105,519, a radiollabelled antagonist for the N-methyl-d-aspartate-associated glycine site, to pig cortical brain membranes. Neurosci Lett 1997;226:79–82

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