AMPA receptor antagonists

Bibliography

• KROGSGAARD-LARSEN P, EBERT B, LUND TM et al: De- sign of excitatory amino acid receptor agonists, partial agonists and antagonists: ibotenic acid as a key lead structure. Eur. J. Med. Chem. (1996) 31:515–537.
   Google Scholar
• LEES GJ: Therapeutic potential of AMPA receptor ligands in neurological disorders. CNS Drugs (1996) 5:51–74.
   Google Scholar
• ••Recent review on therapeutic potential and adverse effectsof AMPA receptor ligands.
   Google Scholar
• BLASCHKE M, GREMMELS D, EVERTS I et al.: Pharma-cological differentiation between neuronal and re-combinant glutamate receptor channel expressed in Xenopus oocytes. Neuropharmacology (1997) 36:1489–1501.
   PubMedGoogle Scholar
• DREJER J: Therapeutic opportunities in modulators ofexcitatory amino acid-mediated neurotransmission. In: Excitatory Amino Acid Receptors: Design of Agonists and Antagonists; Krogsgaard-Larsen P, Hansen JJ (Eds.), Ellis Horwood, Chichester, UK (1992):352–375.
   Google Scholar
• Excitatory Amino Acid Antagonists. Meldrum BS (Ed.),Blackwell, Oxford, UK (1991).
   Google Scholar
• SAUER D, FAGG GE: Excitatory amino acids, excitotox-icity and neurodegenerative disorders. In: Excitatory Amino Acid Receptors: Design of Agonists and Antagonists, Krogsgaard-Larsen P, Hansen JJ (Eds.), Ellis Horwood, Chichester, UK (1992):13–33.
   Google Scholar
• MELDRUM BS: Amino acids as dietary excitotoxins: acontribution to understanding neurodegenerative dis-orders. Brain Research Reviews (1993) 18:293–314.
   PubMedGoogle Scholar
• •An interesting review about naturally occurring amino acids acting as excitotoxins in man.
   Google Scholar
• HOLLMAN M, HEINEMANN S: Cloned glutamate recep-tors. Ann. Rev. Neurosci. (1994) 17:31–108.
   PubMed Web of Science ®Google Scholar
• MOSBACHER J, SCHOEPFER R, MONYER H, BURNASHEVN, SEEBURG PH, RUPPERSBERG JP: A molecular determi-nant for submillisecond desensitation in glutamate re-ceptors. Science (1994) 266:1059–1062.
   PubMed Web of Science ®Google Scholar
• KROGSGAARD-LARSEN P, FERKANY JW, NIELSEN EO et al Novel class of amino acid antagonists at non N-methyl-o-aspartic acid excitatory amino acid receptors. Synthesis, in vitro and in vivo pharmacol-ogy, and neuroprotection. J. Med. Chem. (1991) 34:123–130.
   PubMedGoogle Scholar
• FRANDSEN A, KROGSGAARD-LARSEN P, SCHOUSBOE A: Novel glutamate receptor antagonists selectively pro-tect against kainic acid induced neurotoxicity in cul-tured cerebral cortex neurones. J. Neurochem. (1990) 55:1821–1823.
   PubMedGoogle Scholar
• MADSEN U, BANG-ANDERSEN B, BREHM L et al.: Synthe-sis and pharmacology of highly selective carboxy and phosphono isoxazole amino acid AMPA receptor an-tagonists. J. Med. Chem. (1996) 39:1682–1691.
   PubMed Web of Science ®Google Scholar
• CHRISTENSEN IT, REINHARDT A, NIELSEN B et al.: Excita-tory amino acid agonists and partial agonists. DrugDes. Delivery (1989) 5:57–71.
   Google Scholar
• EBERT B, LENZ SM, BREHM L et al.: Resolution, absolute stereochemistry, and pharmacology of the S-(+)- and R-0-isomers of the apparent partial AMPA receptor agonist (R,S)-2-amino-3-(3-hydroxy-5-phenylisoxazol -4-Apropionic acid [(R,S)-APPA]. J. Med. Chem. (1994) 37:878–884.
   PubMedGoogle Scholar
• EBERT B, MADSEN U, LUND TM, LENZ SM, KROGSGAARD-LARSEN P: Molecular pharmacology of the AMPA agonist (S)-2-amino-3-(3-hydroxy-5-pheny1-4-isoxazoly0propionic acid [(S)-APPA] and the AMPA antagonist, (R)-APPA. Neurochem. Int. (1994) 24:507–515.
   PubMedGoogle Scholar
• HONORE T, DAVIES SN, DREJER J et al.: Quinoxalinedio-nes: potent competitive non-NMDA glutamate recep-tor antagonists. Science (1988) 241:701–703.
   PubMed Web of Science ®Google Scholar
• SHEARDOWN MG, NIELSEN EO, HANSEN AJ, JACOBSEN P, HONORE T: 2,3-Dihydroxy-6-nitro-7-sulfamoyl benzo[4quinoxaline: a neuroprotectant for cerebral ischemia. Science (1990) 247:571–574.
   PubMed Web of Science ®Google Scholar
• OHMORI J, SAKAMOTO S, KUBOTA H et al.: 6-(1H-Imidazol-1-3/0-7-nitro-2,3(111,411)-quinoxalinedione hydrochloride (YM9010 and related compounds: structure-activity relationships for the AMPA-type non-NMDA receptor. J. Med. Chem. (1994) 37: 467–475.
   PubMed Web of Science ®Google Scholar
• OHMORI J, SHIMIZU-SASAMATA M, OKADA M, SAKA-MOTO S: Novel AMPA receptor antagonists: synthesis and structure-activity relationship of 1-hydroxy-7- (1H-imidazol-1-3/0-6-nitro-2,3 (111,411)-quinoxalin-edione and related compounds. J. Med. Chem. (1996) 39:3971–3979.
   PubMed Web of Science ®Google Scholar
• •Focus on structural requirements for AMPA receptor affinity.
   Google Scholar
• OHMORI J, KUBOTA H, SHIMIZU-SASAMATA M, OKADA M, SAKAMOTO S: Novel a-amino-3-hydroxy-5-methyl--4-isoxazole propionate receptor antagonists: synthe-sis and structure-activity relationship of 6-(1H-imidazol-1-y1)-7-nitro-2,3 (111,41)-pyrido[2,3-b]pyrazinedione and related compounds. J. Med. Chem. (1996) 39:1331–1338.
   PubMed Web of Science ®Google Scholar
• CAI SX, HUANG JC, ESPITIA SA et al.: 5-(N-Oxyaza)-7--substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antago-nists for NMDA/glycine, AMPA and kainate receptors. J. Med. Chem. (1997) 40:3679–3686.
   PubMed Web of Science ®Google Scholar
• BIGGE CF, MALONE TC, BOXER PA et al.: Synthesis of 1,4,7,8,9,10-hexahydro-9-methy1-6-nitropyrido[3,44] quinoxaline-3,4-diones: characterization of a-amino--3-hydroxy-5-methy1-4-isoxazole propionic acid (and N-methyl-n-aspartate) receptor and anticonvulsant ac-tivity. J. Med. Chem. (1995) 38:3720–3740.
   PubMedGoogle Scholar
• ••Paper in which numerous quinoxalinediones are combinedand analysed via QSAR in order to facilitate the design of new AMPA receptor antagonists.
   Google Scholar
• OHMORI J, SHIMIZU-SASAMATA M, OKADA M, SAKA-MOTO S: 8-(1H-Imidazol-1-y0-7-nitro-4(51)-im-idazo[1,2-a]quinoxalinone and related compounds: synthesis and structure-activity relationship for the AMPA-type non-NMDA receptor. J. Med. Chem. (1997) 40:2053–2063.
   PubMedGoogle Scholar
• ••Report on quinoxalinediones in which a pharmacophoremodel of AMPA receptor is suggested on the basis of previ-ous studies.
   Google Scholar
• WATJEN F, NIELSEN E0, DREJER J, JENSEN LH: Isatin oxi-mes - a novel series of bioavailable non-NMDA antago-nists. Bioorg. Med. Chem. Lett. (1993) 3:105–106.
   Google Scholar
• JOHANNSEN TH, DREJER J, WATJEN F, NIELSEN 0: A novel non-NMDA receptor antagonist shows selective displacement of low-affinity [311]kainate binding. Eur. Pharmacol. (1993) 246:195–204.
   PubMedGoogle Scholar
• WATJEN F, BIGGE CF, JENSEN LH et al.: NS 257 [1,2,3,6,7,8-hexahydro-3-(hydroxymino)-N,N,7-trimethy1-2-oxobenzo[2,1-b:3,4-0dipyrrole-5-sulfonamide] is a potent, systemically active AMPA re-ceptor antagonist. Bioorg. Med. Chem. Lett. (1994) 3:371–376.
   Google Scholar
• CARLING RW, LEESON PD, MOORE KW et al: 3-Nitro-3,4-dihydro-2(11-4-quinolones. Excitatory amino acid an-tagonists acting at glycine-site NMDA and (R5)-a-amino-3-hydroxy-5-methy1-4-isoxazole propi-onic acid receptors. J. Med. Chem. (1993) 36:3397–3408.
   Google Scholar
• CORDI AA, DESOS P, RANDLE JCR, LEPAGNOL J: Structure-activity relationships in a series of 3-sulfonylamino-2(11-4-quinolones as new AMPA/kai-nate and glycine antagonists. Bioorg. Med. Chem. Lett. (1995) 3:129–141.
   Google Scholar
• DESOS P, LEPAGNOL JM, MORAIN P, LESTAGE P, CORDIAA: Structure-activity relationships in a series of 2(111)-quinolones bearing different acidic function in the 3-position: 6,7-dichloro-2(11-)-oxoquinoline-3--phosphonic acid, a new potent and selective AMPA/kainate antagonist with neuroprotective prop-erties. J. Med. Chem. (1996) 39:197–206.
   PubMed Web of Science ®Google Scholar
• ORNSTEIN PL, ARNOLD MB, AUGENSTEIN NK, LODGE D,LEANDER JD, SCHOEPP DD: (3SR,4aRS,6RS,8aRS)-6-[2-(1H-Tetrazoly1-5-yOethyl]decahydroisoquinoline-3-carboxylic acid: a structurally novel, systemically ac-tive, competitive AMPA receptor antagonist. J. Med. Chem. (1993) 36:2046–2048.
   PubMedGoogle Scholar
• ORNSTEIN PL, ARNOLD MB, ALLEN NK et al.:(3SR,4aRS,6RS,8aR,S)-6-(1H-Tetrazoly1-5--yOdecahydroisoquinoline-3-carboxylic acid, a novel, competitive, systemically active NMDA and AMPA re-ceptor antagonist. J. Med. Chem. (1995) 38:4885–4890.
   PubMedGoogle Scholar
• CLARKE VR, BALLYK BA, HOO KH et al.: A hippocampal G1uR5 kainate receptor regulating inhibitory synaptic transmission. Nature (1997) 389:599–603.
   PubMed Web of Science ®Google Scholar
• RASMUSSEN K, KENDRICK WT, KOGAN JH, AGHAJANIAN GK: A selective AMPA antagonists, LY 293558, sup-presses morphine withdrawal-induced activation of locus coeruleus neurons and behavioral signs of mor-phine withdrawal. Neuropsychopharmacology (1996) 15:497–505.
   PubMedGoogle Scholar
• SCHOEPP DD, SALHOFF CR, FUSON KS, SACAAN AT, TIZ-ZANO JP, ORNSTEIN PL: Selective protection against AMPA- and kainate-evoked neurotoxicity by (35,4 a R, 6 R, 8-6-aR)[2- (1 H-Tetr az olyl- 5--3/1) ethyl] decahydrois oquinoline -3-carboxylic acid (-)LY 293558 and its racemate LY 215490. J. Neural Transm. (1996) 103:905–906.
   PubMedGoogle Scholar
• ORNSTEIN PL, ARNOLD MB, ALLEN NK et al: Structure-activity studies of 6- (tetrazolylalkyl)-substituted decahydroisoquinoline-3-carboxylic acid AMPA re-ceptor antagonists. 1. Effects of stereochemistry, chain length and chain substitution. J. Med. Chem. (1996) 39:2219–2231.
   Google Scholar
• ••With [36], two papers in which the influence of substitutionand stereochemistry on in vivo and in vitro activity of deca-hydroisoquinoline derivatives is discussed.
   Google Scholar
• ORNSTEIN PL, ARNOLD MB, ALLEN NK et al.: Structure- activity studies of 6-substituted decahydro isoquinoline-3-carboxylic acid AMPA receptor antago-nists. 2. Effects of distal acid bioisosteric substitution, absolute stereochemical preferences and in vivo activ-ity. J. Med. Chem. (1996) 39:2232–2244.
   Google Scholar
• ROGAWSKI MA: Therapeutic potential of excitatory amino acid antagonists: channel blockers and 2,3-benzodiazepines. Trends Pharmacol. Sci. (1993) 14:325–331.
   PubMed Web of Science ®Google Scholar
• •Starting-line for the development of numerous and interest-ing 2,3-benzodiazepine derivatives as non-competitive AMPA antagonists.
   Google Scholar
• VIZI ES, MIKE A, TARNAWA I: 2,3-Benzodiazepines (GYKI 52466 and analogues): negative allosteric modulators of AMPA receptors. CNS Drugs Rev. (1996) 2:91–126.
   Google Scholar
• PARTIN KM, MAYER ML: Negative allosteric modulation of wild-type and mutant AMPA receptors by GYKI 53655. Mol. Pharmacol (1996) 49:142–148.
   PubMed Web of Science ®Google Scholar
• DONEVAN SD, ROGAWSKI MA: Allosteric regulation of alpha-amino- 3 -hydroxy- 5 -methyl- 4 - isoxazolepropionate by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines. Neuroscience (1998) 87:615–629.
   PubMedGoogle Scholar
• SMITH SE, DURMULLER N, MELDRUM BS: The non-N-methyl-o-aspartate receptor antagonists, GYKI 52466 and NBQX are anticonvulsant in two animal models of reflex epilepsy. Eur. j Pharmacol (1991) 201:179–183.
   PubMed Web of Science ®Google Scholar
• DONEVAN SD, ROGAWSKI MA: GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/kainate receptor responses. Neu-ron (1993) 10:51–59.
   Google Scholar
• CHAPMAN AG, AL-ZUBAIDY Z, MELDRUM BS: Ani-racetam reverses the anticonvulsant action of NBQX and GYKI 52466 in DBA/2 mice. Eur. J. Pharmacol (1993) 231:301–303.
   PubMed Web of Science ®Google Scholar
• LOSCHER WR, HONACK D: Effects of the non-NMDA an-tagonists NBQX and GYKI 52466 on different seizures types in mice: comparison with diazepam and interac-tion with flumazenil. Br. J. Pharmacol (1994) 113:1349–1357.
   PubMedGoogle Scholar
• PARSON CG, GRUNER R, ROZENTAL J: Comparative patch clamp studies on the kinetics and selectivity of glutamate receptor antagonism by 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(Dquinoxaline (NBQX) and 1- (4-aminopheny1)-4-methy1-7,8-methylenedioxy-511-2,3-benzodiazepine (GYKI 52466). Neuropharmacol-ogy (1994) 33:589–604.
   PubMedGoogle Scholar
• TARNAWA I, BERZSENYI P, ANDRASI F et al.: Structure-activity relationships of 2,3-benzodiazepine com-pounds with glutamate antagonistic action. Bioorg. Med. Chem. Lett. (1993) 3:99–104.
   Google Scholar
• DONEVAN SD, YAMAGUCHI SI, ROGAWSKI MA: Non-N-methyl-o-aspartate receptor antagonism by 3-N-substituted 2,3-benzodiazepines: relationship to anti-convulsant activity. J. Pharmacol Exp. Ther. (1994) 271:25–29.
   PubMedGoogle Scholar
• WILDING JT, HUETTNER JE: Differential antagonism of a-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid-preferring and kainate-preferring receptor by 2,3-benzodiazepines. Mol Pharmacol (1995) 47:582–587.
   PubMed Web of Science ®Google Scholar
• ANDERSON BA, HANSEN MM, HARKNESS AR et al.: Appli-cation of a practical biocatalytic reduction to an enan-tioselective synthesis of the 511–2,3-benzodiazepine LY 300164.1 Am. Chem. Soc. (1995) 117:12358–12359.
   Google Scholar
• LODGE D, BOND A, O'NEILL M, HICKS CA, JONES MG: Stereoselective effects of 2,3-benzodiazepines in vivo: electrophysiology and neuroprotection studies. Neu-ropharmacology (1996) 35: 1681-1688.
   Google Scholar
• BLEAKMAN D, BALLYK BA, SCHOEPP DD et al.: Activity of 2,3-benzodiazepines at native rat and recombinant human glutamate receptors in vitro: stereospecificity and selectivity profiles. Neuropharmacology (1996) 35: 1689-1702.
   Google Scholar
• DE SARRO G, CHIMIRRI A, DE SARRO A et al: GYKI 52466and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice. Eur. J. Pharmacol. (1995) 294:411–422.
   PubMed Web of Science ®Google Scholar
• CHIMIRRI A, DE SARRO G, DE SARRO A et al: 1-Ary1-3,5- dihydro-41-1-2,3-benzodiazepin-4-ones: novel AMPA receptor antagonists. J. Med. Chem. (1997) 40:1258–1269.
   PubMed Web of Science ®Google Scholar
• •Report in which some structural modifications afforded compounds generally less toxic and with longer lasting anti-convulsant effects than those of previously reported 2,3-benzodiazepine derivatives.
   Google Scholar
• DE SARRO G, RIZZO M, SINOPOLI VA et al.: Relationship between anticonvulsant activity and plasma level of some 2,3-benzodiazepines in genetically epilepsy prone rats. Pharmacol. Biochem. Behav. (1998) 61:215–220.
   PubMed Web of Science ®Google Scholar
• DE SARRO A, DE SARRO G, GITTO R et al.: 7,8-Methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists. Bioorg. Med. Chem. Lett. (1998) 8:971–976.
   PubMedGoogle Scholar
• WANG Y, KONKOY CS, ILYIN VI et al.: Synthesis of 7,8- (methylenedioxy)-1-phenyl-3,5-dihydro-411-2,3-benzodiazepin-4-ones as novel and potent noncom-petitive AMPA receptor antagonists. J. Merl. Chem. (1998) 41:2621–2625.
   PubMedGoogle Scholar
• CHIMIRRI A, DE SARRO G, DE SARRO A et al.: 3,5-Dihydro-4H-2,3-benzodiazepine-4-thiones: a new class of AMPA receptor antagonists./ Med. Chem. (1998) 41:3409–3416.
   Google Scholar
• PELLETIER JC, HESSON DP, JONES KA, COSTA AM: Substi-tuted 1,2-dihydrophthalazines: potent, selective, and noncompetitive inhibitors of the AMPA receptor. J. Merl. Chem. (1996) 39:343–346.
   PubMed Web of Science ®Google Scholar
• HESSON DP, STURGESS MA: Homology modeling of the AMPA receptor: a quantitative predictive tool for the design of novel antagonists. Bioorg. Med. Chem. Lett. (1997) 7:1437–1442.
   Google Scholar
• •Employing the concept of homology modelling, a predictive model of the AMPA receptor has been generated.
   Google Scholar