New trends in the development of AMPA receptor antagonists

Bibliography

• DINGLEDINE R, BORGES K, BOWIE D, TRAYNELIS SF: The glutamate receptor ion channels. Pharmacol Rev. (1999) 51 (1) :7–61.
   PubMed Web of Science ®Google Scholar
• JINGAMI H, NAKANISHI S, MORIKAWA K: Structure of the metabotropic glutamate receptor. Carr: Opin. Neurobiol (2003) 13(3):271–278.
   PubMedGoogle Scholar
• LEES GJ: Pharmacology of AMPA/kainate receptor ligands and their therapeutic potential in neurological and psychiatric disorders. Drugs (2000) 59 (1):33–78.
   PubMed Web of Science ®Google Scholar
• STONE TW, ADDAE JI: The pharmacological manipulation of glutamate receptors and neuroprotection. Ear. Pharmacol (2002) 447(2-3):285–296.
   PubMed Web of Science ®Google Scholar
• ROSENMUND C, STERN-BACH Y, STEVENS CF: The tetrameric structure of a glutamate receptor channel. Science (1998) 280(5369):1596–1599.
   PubMed Web of Science ®Google Scholar
• SUTCLIFFE MJ, WO ZG, OSWALD RE: Three-dimensional models of non-NMDA glutamate receptors. Biophys. J. (1996) 70(4):1575–1589.
   PubMedGoogle Scholar
• SUTCLIFFE MJ, SMEETON AH, WO ZG, OSWALD RE: Three-dimensional models of glutamate receptors. Biochem. Soc. Trans. (1998) 26(3):450–458.
   PubMedGoogle Scholar
• HOGNER A, GREENWOOD JR, LILJEFORS T et al: Competitive antagonism of AMPA receptors by ligands of different classes: crystal structure of ATPO bound to the G1uR2 ligand-binding core, in comparison with DNQX. .1. Med. Chem. (2003) 46 (2):214–221.
   Google Scholar
• ARMSTRONG N, GOUAUX E: Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: crystal structures of the G1uR2 ligand binding core. Neuron (2000) 28(1):165–181.
   PubMed Web of Science ®Google Scholar
• CHIMIRRI A, GITTO R, ZAPPALA M: AMPA receptor antagonists. Expert Opin. The]: Patents (1999) 9(5):557–570.
   Web of Science ®Google Scholar
• CORDI AA, DESOS P, RUANO E et al.: Novel quinolinone-phosphonic acid AMPA antagonists devoid of nephrotoxicity. Farmaco (2002) 57 (10):787–802.
   PubMedGoogle Scholar
• •Example of a water-soluble AMPA antagonist.
   Google Scholar
• NAKANO M, UEDA H, LI JY, MATSUMOTO M, YANAGIHARA T: A potent AMPA/kainate receptor antagonist, YM-90K, attenuates the loss of N-acetylaspartate in the hippocampal CA1 area after transient unilateral forebrain ischemia in gerbils. Life ScL (2001) 69(17):1983–1990.
   PubMed Web of Science ®Google Scholar
• NIKAM SS, KORNBERG BE: AMPA receptor antagonists. C11171 Med. Chem. (2001) 8(2):155–170.
   Google Scholar
• TURSKI L, HUTH A, SHEARDOWN M et al.: ZK-200775: a phosphonate quinoxalinedione AMPA antagonist for neuroprotection in stroke and trauma. Proc. Natl. Acad. Sci. USA (1998) 95 (18):10960–10965.
   PubMed Web of Science ®Google Scholar
• ELTING JW, SULTER GA, KASTE M et al: AMPA antagonist ZK200775 in patients with acute ischemic stroke: possible glial cell toxicity detected by monitoring of 5-100B serum levels. Stroke (2002) 33 (12):2813–2818.
   PubMedGoogle Scholar
• TURSKI L, SCHNEIDER HH, NEUHAUS R et al: Phosphonate quinoxalinedione AMPA antagonists. Restor. Neurol. Neurosci. (2000) 17(1):45–59.
   PubMedGoogle Scholar
• TAKANO Y, SHIGA F, ASANO J, ANDO N, UCHIKI H, ANRAKU T: Synthesis and AMPA receptor antagonistic activity of a novel class of quinoxalinecarboxylic acid with a substituted phenyl group at the C-7 position. Bioorg. Med. Chem. Lett(2003) 13(20):3521–3525.
   PubMedGoogle Scholar
• VARANO F, CATARZI D, COLOTTA V et al.: Synthesis, glycine/NMDA and AMPA binding activity of some new 2,5,6-trioxopyrazino[12,3-delquinoxalines and of their restricted analogs 2,5-dioxo- and 4,5-dioxoimidazo [1,5, 4-del quinoxalines. Arch. Pharm. (Weinheim) (1999) 332(6) :201–207.
   PubMedGoogle Scholar
• CATARZI D, COLOTTA V, VARANO F et al.: 7-Chloro-4,5-dihydro-8- (1,2,4-triazol 4 yl) 4 oxo 1,2,4 triazolo [1, 5-alquinoxaline-2- carboxylates as novel highly selective AMPA receptor antagonists. .1. Med. Chem. (2000) 43(21):3824–3826.
   Google Scholar
• CATARZI D, COLOTTA V, VARANO F et al.: Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroary1-4-oxo-1,2,4-triazolo[1,5-a[quinoxaline-2-carboxylates analogues of TQX-173. J. Med. Chem. (2001) 44 (19):3157–3165.
   PubMedGoogle Scholar
• CATARZI D, COLOTTA V, VARANO F et al.: Synthesis and biological evaluation of analogues of 7-chloro-4,5-dihydro-4- oxo-8- (1,2,4-triazol-4-y1)-1,2,4-triazolo [1, 5-a[quinoxaline-2-carboxylic acid (TQX-173) as novel selective AMPA receptor antagonists. J. Med. Chem. (2004) 47(1):262–272.
   PubMedGoogle Scholar
• VARANO F, CATARZI D, COLOTTA V et al.: Synthesis and biological evaluation of a new set of pyrazolo[1,5-c]quinazoline-2-carboxylates as novel excitatory amino acid antagonists. J. Med. Chem. (2002) 45(5):1035–1044.
   PubMedGoogle Scholar
• •Focus on the structural requirements for AMPA receptor selectivity.
   Google Scholar
• COLOTTA V, CATARZI D, VARANO F et al.: 3-Hydroxy-quinazoline-2,4-dione as a useful scaffold to obtain selective Gly/ NMDA and AMPA receptor antagonists. Bioorg. Med. Chem. Lett (2004) 14(9):2345–2349.
   PubMedGoogle Scholar
• MIGNANI S, BOHME GA, BOIREAU A et al.: 8-Methylureido-4,5-dihydro-4-oxo-10H-imidazo [1, 2-a] indeno [1, 2-e] pyrazines: highly potent in vivo AMPA antagonists. Bioorg. Med. Chem. Lett. (2000) 10(6):591–596.
   PubMedGoogle Scholar
• STUTZMANN JM, BOHME GA, BOIREAU A et al: 4,10-Dihydro-4-oxo-4H-imidazo [1,2-a]indeno [1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with in vivo activity. Bioorg. Med. Chem. Lett. (2000) 10(10):1133–1137.
   PubMed Web of Science ®Google Scholar
• JIMONET P, CHEVE M, BOHME GA et al.: 8-Methylureido- 10-amino- 10-methyl-imidazo [1,2-a]indeno [1,2-e] pyrazine-4-ones: highly in vivo potent and selective AMPA receptor antagonists. Bioorg. Med. Chem. (2000) 8(8):2211–2217.
   PubMedGoogle Scholar
• PRATT J, JIMONET P, BOHME GA et al.: Synthesis and potent anticonvulsant activities of 4-oxo-imidazo [1,2-indeno [1, 2-e]pyrazin-8- and -9-carboxylic (acetic) acid AMPA antagonists. Bioorg. Med. Chem. Lett (2000) 10(202749–2754.
   Google Scholar
• JIMONET P, BOHME GA, BOUQUEREL J et al.: Bioisosteres of 9-carboxymethy1-4-oxo-imidazo [1,2-a]indeno- [1,2-e]pyrazin-2-carboxylic acid derivatives. Progress towards selective, potent in vivo AMPA antagonists with longer durations of action. Bioorg. Med. Chem. Lett. (2001) 11(2):127–132.
   Google Scholar
• STUTZMANNJM, BOHME GA, BOIREAU A et al.: Synthesis of anticonvulsive AMPA antagonists: 4-oxo-10-substituted-imidazo[1,2-a]indeno [1,2-e]pyrazin-2-carboxylic acid derivatives. Bioorg. Med. Chem. Lett(2001) 11(9):1205–1210.
   PubMedGoogle Scholar
• MIGNANI S, BOHME GA, BIRRAUX G et al.: 9-Carboxymethy1-5H,10H- imidazo [1, 2-a] indeno [1, 2-e]pyrazin-4-one-2-carbocyl ic acid (RPR-117824): selective anticonvulsive and neuroprotective AMPA antagonist. Bioorg. Med. Chem. (2002) 10(5):1627–1637.
   PubMed Web of Science ®Google Scholar
• MORE JC, TROOP HM, DOLMAN NP, JANE DE: Structural requirements for novel willardiine derivatives acting as AMPA and kainate receptor antagonists. Br: J. Pharmacol (2003) 138(6):1093–1100.
   PubMedGoogle Scholar
• SAVIDGE JR, BRISTOW DR: Ca2+ permeability and joro spider toxin sensitivity of AMPA and kainate receptors on cerebellar granule cells. Eur. Pharmacol (1998) 351(1):131–138.
   PubMedGoogle Scholar
• KOIKE M, IINO M, OZAWA S: Blocking effect of 1-naphthyl acetyl spermine on Ca2±-permeable AMPA receptors in cultured rat hippocampal neurons. Neurosci. Res. (1997) 29(1):27–36.
   PubMedGoogle Scholar
• YONEDA Y, KAWAJIRI S, HASEGAWA A et al.: Synthesis of polyamine derivatives having non-hypotensive Ca2+-permeable AMPA receptor antagonist activity. Bioorg. Med. Chem. Lett (2001) 11(10):1261–1264.
   PubMedGoogle Scholar
• YONEDA Y, KAWAJIRI S, SUGIMURA M et al: Synthesis of diaminobutane derivatives as potent Ca2+-permeable AMPA receptor antagonists. Bioorg. Med. Chem. Lett (2001) 11(19):2663–2666.
   PubMedGoogle Scholar
• YONEDA Y, MIMURA T, KAWAGOE K et al.: Discovery of diaminobutane derivatives as Ca2±-permeable AMPA receptor antagonists. Bioorg. Med. Chem. (2002) 10(5):1347–1359.
   PubMedGoogle Scholar
• KROMANN H, KRIKSTOLAITYTE S, ANDERSEN AJ et al.: Solid-phase synthesis of polyamine toxin analogues: potent and selective antagonists of Ca2+-permeable AMPA receptors. J. Med. Chem. (2002) 45(26):5745–5754.
   PubMedGoogle Scholar
• DONEVAN SD, ROGAWSKI MA: GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/kainate receptor responses. Neuron (1993) 10(1):51–59.
   PubMed Web of Science ®Google Scholar
• DONEVAN SD, YAMAGUCHI S, ROGAWSKI MA: Non-N-methyl-D-aspartate receptor antagonism by 3-N-substituted 2,3-benzodiazepines: relationship to anticonvulsant activity. Pharmacol Exp. Ther. (1994) 271(1):25–29.
   PubMedGoogle Scholar
• ANDRASI F: Talampanel. Antiepileptic, neuroprotectant, skeletal muscle relaxant. Drugs Fut. (2001) 26(8):754–756.
   Google Scholar
• RUEL J, GUITTON MJ, PUELL JL: Negative allosteric modulation of AMPA-preferring receptors by the selective isomer GYKI 53784 (LY303070), a specific non-competitive AMPA antagonist. CNS Drug Rev (2002) 8(3):235–254.
   PubMedGoogle Scholar
• SZABADOS T, GIGLER G, GACSALYI I, GYERTYAN I, LEVAY G: Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain Res. Bull. (2001) 55(3):387–391.
   PubMed Web of Science ®Google Scholar
• VILAGI I, TAKACS J, GULYAS -KOVACS A, BANCZEROWSKI-PELYHE I, TARNAWA I: Protective effect of the antiepileptic drug candidate talampanel against AMPA-induced striatal neurotoxicity in neonatal rats. Brain Res. Bull. (2002) 59(1):35–40.
   PubMedGoogle Scholar
• BEVACQUA F, BASSO A, GITTO R, BRADLEY M, CHIMIRRI A: Solid-phase Friedel-Crafts acylation on polystyrene resins-synthesis of antiepiletic 1-ary1-3,5-dihydro-4H-2,3-benzodiazepin-4-ones. Tetrahedron Lett. (2001) 42(43):7683–7685.
   Google Scholar
• •The first solid-phase synthesis of 2,3-benzodiazepines.
   Google Scholar
• HAMORI T, SOLYOM S, BERZSENYI P, ANDRASI F, TARNAWA I: Structural analogues of some highly active non-competitive AMPA antagonists. Bioorg. Med. Chem. Lett. (2000) 10(9):899–902.
   PubMedGoogle Scholar
• GITTO R, ZAPPAL M, DE SG, CHIMIRRI A: Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists. Farmaco (2002) 57(2):129–134.
   PubMedGoogle Scholar
• SOLYOM S: Research on new AMPA antagonists of 2,3-benzodiazepine type. Pharmazie (2001) 56\(Supp1.1)S62–66.
   Google Scholar
• GRASSO S, DE SARRO G, DE SARRO A et al.: Synthesis and anticonvulsant activity of novel and potent 1-ary1-7,8-methylenedioxy-1,2,3,5-tetrahydro-4H-2,3-benzodiazepin-4-ones. Bioorg. Med. Chem. Lett(2001) 11(4):463–466.
   Google Scholar
• DE SARRO G, CHIMIRRI A, MELDRUM BS: Group III mGlu receptor agonists potentiate the anticonvulsant effect of AMPA and NMDA receptor block. Eur. Pharmacol (2002) 451(1):55–61.
   PubMedGoogle Scholar
• ABRAHAM G, SOLYOM S, CSUZDI E et al.: New non competitive AMPA antagonists. Bioorg. Med. Chem. (2000) 8(8):2127–2143.
   PubMed Web of Science ®Google Scholar
• ZAPPALA M, GITTO R, BEVACQUA F et al.: Synthesis and evaluation of pharmacological and pharmacokinetic properties of 11H-, 2,4]triazolo[4,5-ci5-[2,31benzodiazepin-3(2H)-ones. Med. Chem. (2000) 43(25):4834–4839.
   Google Scholar
• CHIMIRRI A, GITTO R, QUARTARONE S, ORLANDO V, DE SARRO A, DE SARRO GB: Synthesis and pharmacological properties of new 3- ethoxycarbonyl-11 H- [1, 2,4]triazolo [4, 5-c][2,31benzodiazepines. Farmaco (2002) 57(9):759–763.
   PubMedGoogle Scholar
• GITTO R, ORLANDO V, QUARTARONE S et al.: Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives. Med. Chem. (2003) 46(17):3758–3761.
   Google Scholar
• RZESKI W, IKONOMIDOU C, TURSKI L: Glutamate antagonists limit tumor growth. Biochem. Pharmacol (2002) 64(8):1195–1200.
   PubMedGoogle Scholar
• PEI XF, STURGESS MA, VALENZUELA CF, MACCECCHINI ML: Allosteric modulators of the AMPA receptor: novel 6-substituted dihydrophthalazines. Bioorg. Med. Chem. Lett. (1999) 9(4):539–542.
   PubMedGoogle Scholar
• PELLETIER JC, HESSON DP, JONES KA, COSTA AM: Substituted 1,2-dihydrophthalazines: potent, selective, and noncompetitive inhibitors of the AMPA receptor. I Med. Chem. (1996) 39(2):343–346.
   PubMed Web of Science ®Google Scholar
• LI BQ, PEI XF, MACCECCHINI M: Novel sulfur containing dihydrophthalazine antagonists of AMPA receptors. 220th ACS Meeting. Washington DC, USA (2000) MEDI 212.
   Google Scholar
• GITTO R, CHIMIRRI A, ZAPPALA M, DE SARRO G, DE SARRO A: Synthesis and pharmacological evaluation of 4-aryl-6, 7-dimethoxyphthalazines as anticonvulsant agents. Med. Chem. Res. (2000) 10(1):1–10.
   Google Scholar
• GRASSO S, DE SARRO G, DE SARRO A et al.: Synthesis and anticonvulsant activity of novel and potent 6,7-methylenedioxyphthalazin-1(2H)-ones. Med . Chem. (2000) 43 (15):2851–2859.
   Google Scholar
• CHENARD BL, WELCH WM, BLAKE JF et al.: Quinazolin-4-one alpha-amino-3-hydroxy-5-methy1-4-isoxazolepropionic acid (AMPA) receptor antagonists: structure-activity relationship of the C-2 side chain tether.' Med. Chem. (2001) 44(11):1710–1717.
   Google Scholar
• CHENARD BL, MENNITI FS, PAGNOZZI MJ, SHENK KD, EWING FE, WELCH WM: Methaqualone derivatives are potent noncompetitive AMPA receptor antagonists. Bioorg. Med. Chem. Lett. (2000) 10(11):1203–1205.
   PubMedGoogle Scholar
• MENNITI FS, BUCHAN AM, CHENARD BL et al: CP-465,022, a selective noncompetitive AMPA receptor antagonist, blocks AMPA receptors but is not neuroprotective in vivo. Stroke (2003) 34(1):171–176.
   PubMedGoogle Scholar
• LAZZARO JT, PATERNAIN AV, LERMA J et al.: Functional characterization of CP-465,022, a selective, noncompetitive AMPA receptor antagonist. Neuropharmacology (2002) 42(2):143–153.
   PubMedGoogle Scholar
• WELCH WM, EWING FE, HUANG J et al.: Atropisomeric quinazolin-4-one derivatives are potent noncompetitive a-amino-3-hydroxy-5-methy1-4-isoxazolepropionic acid (AMPA) receptor antagonists. Bioorg. Med. Chem. Lett (2001) 11 (2):177–181.
   PubMedGoogle Scholar
• MENNITI FS, CHENARD BL, COLLINS MB et al.: Characterization of the binding site for a novel class of noncompetitive a-amino-3-hydroxy-5-methy1-4-isoxazolepropionic acid receptor antagonists. Mot. PharmacoL (2000) 58(6):1310–1317.
   PubMedGoogle Scholar
• OHNO K, TSUTSUMI R, MATSUMOTO N et al.: Functional characterization of YM928, a novel moncompetitive a-amino-3-hydroxy-5-methy1-4-isoxazolepropionic acid (AMPA) receptor antagonist.' Pharmacol Exp. Ther. (2003) 306 (1):66–72.
   Google Scholar
• YAMASHITA H, OHNO K, AMADA Y et al.: Effects of 2- [N-(4-chloropheny1)-N-methylamino1-4H-pyrido[3.2-e1-1,3-thiazin-4-one (YM928), an orally active a-amino-3-hydroxy-5-methy1-4-isoxazolepropionic acid receptor antagonist, in models of generalized epileptic seizure in mice and rats. j. Pharmacol Exp. Ther. (2004) 308(1):127–133.
   Google Scholar
• FEIGIN V: Irampanel Boehringer Ingelheim. Carr. Opin. Livestig. Drugs (2002) 3(6):908–910.
   PubMedGoogle Scholar
• WIENRICH M, BRENNER M, LOSCHER W et al: In vivo pharmacology of BIIR-561 CL, a novel combined antagonist of AMPA receptors and voltage-dependent Na+ channels. Br. J. Pharmacol (2001) 133(6):789–796.
   PubMed Web of Science ®Google Scholar
• •Example of combination of actions in one molecule.
   Google Scholar
• WEISER T, WIENRICH M, BRENNER M, KUBIAK R, WECKESSER G, PALLUK R The AMPA receptor/Na+ channel blocker BIIR-561 CL is protective in a model of global cerebral ischaemia. Eur. Pharmacol (2001) 421(3):165–170.
   PubMed Web of Science ®Google Scholar
• GITTO R, BARRECA ML, DE LUCA L et al.: Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist. Med. Chem. (2003) 46(1):197–200.
   Google Scholar
• •A new class of potent rationally designed non-competitive AMPA antagonists.
   Google Scholar
• GITTO R, CARUSO R, ORLANDO V et al.: Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives. Farmaco (2004) 59(1):7–12.
   PubMedGoogle Scholar
• FERRERI G, CHIMIRRI A, RUSSO E et al.: Comparative anticonvulsant activity of N-acety1-1-ary1-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives in rodents. Pharmacol Biochem. Behav. (2004) 77(1):85–94.
   PubMed Web of Science ®Google Scholar
• DE LUCA L, MACCHIARULO A, COSTANTINO G et al.: Binding modes of noncompetitive AMPA antagonists: a computational approach. Farmaco (2003) 58(2):107–113.
   PubMedGoogle Scholar
• BARRECA ML, GITTO R, QUARTARONE S, DE LUCA L, DE SARRO G, CHIMIRRI A: Pharmacophore modeling as an efficient tool in the discovery of novel noncompetitive AMPA receptor antagonists. I Chem. hal Comput. Sci. (2003) 43(2):651–655.
   PubMedGoogle Scholar
• •3D-pharmacophore model obtained by using compounds selected from different structural classes of non-competitive AMPA antagonists.
   Google Scholar
• MACCHIARULO A, DE LUCA L, COSTANTINO G et al.: QSAR study of anticonvulsant negative allosteric modulators of the AMPA receptor. I Med. Chem. (2004) 47(7):1860–1863.
   PubMed Web of Science ®Google Scholar
• JACKSON A, MEAD AN, STEPHENS DN: Behavioural effects of alpha-amino-3-hydroxy-5-methy1-4-isoxazolepropionate-receptor antagonists and their relevance to substance abuse. Pharmacol. Ther: (2000) 88(1):59–76.
   PubMedGoogle Scholar