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Volumn 43, Issue 15, 2000, Pages 2851-2859

Synthesis and anticonvulsant activity of novel and potent 6,7- methylenedioxyphthalazin-1(2H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 AMINOPHENYL) 3,4 DIHYDRO 4 METHYL 3 METHYLCARBAMOYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; 1 (4 AMINOPHENYL) 4 METHYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; 4 (4 AMINOPHENYL) 2 BUTYLCARBAMOYL 6,7 METHYLENEDIOXYPHTHALAZIN 1(2H) ONE; 4 (4 AMINOPHENYL) 6,7 METHYLENEDIOXYPHTHALAZIN 1(2H) ONE; ANIRACETAM; ANTICONVULSIVE AGENT; PHTHALAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034721136     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm001002x     Document Type: Article
Times cited : (239)

References (43)
  • 4
    • 0028865828 scopus 로고
    • (3SR,4aRS,6SR,8aRS)-6-(1H-Tetrazol-5-yl)decahydrosoquinoline-3-carboxylic acid, a novel, competitive, systemically active NMDA and AMPA receptor antagonist
    • Ornstein, P. L.; Arnold, M. B.: Allen, N. K.; Leander, J. D.; Tizzano, J. P.; Lodge, D.; Schoepp, D. D. (3SR,4aRS,6SR,8aRS)-6-(1H-Tetrazol-5-yl)decahydrosoquinoline-3-carboxylic Acid, a Novel, Competitive, Systemically Active NMDA and AMPA Receptor Antagonist. J. Med. Chem. 1995, 38, 4885-4890.
    • (1995) J. Med. Chem. , vol.38 , pp. 4885-4890
    • Ornstein, P.L.1    Arnold, M.B.2    Allen, N.K.3    Leander, J.D.4    Tizzano, J.P.5    Lodge, D.6    Schoepp, D.D.7
  • 5
    • 0025789026 scopus 로고
    • The anticonvulsant effect of the non-NMDA antagonists, NBQX and GYKI 52466, in mice
    • (a) Chapman, A. G.; Smith, S. E.; Meldrum, B. S. The Anticonvulsant Effect of the Non-NMDA Antagonists, NBQX and GYKI 52466, in Mice. Epilepsy Res. 1991, 9, 92-96.
    • (1991) Epilepsy Res. , vol.9 , pp. 92-96
    • Chapman, A.G.1    Smith, S.E.2    Meldrum, B.S.3
  • 6
    • 0025884961 scopus 로고
    • The non-N-methyl-D-aspartate receptor antagonists, GYKI 52466 and NBQX are anticonvulsant in two animal models of reflex epilepsy
    • (b) Smith, S. E.; Durmuller, N.; Meldrum, B. S. The Non-N-Methyl-D-Aspartate Receptor Antagonists, GYKI 52466 and NBQX are Anticonvulsant in two Animal Models of Reflex Epilepsy. Eur. J. Pharmacol. 1991, 201, 179-183.
    • (1991) Eur. J. Pharmacol. , vol.201 , pp. 179-183
    • Smith, S.E.1    Durmuller, N.2    Meldrum, B.S.3
  • 7
    • 0027942174 scopus 로고
    • Non-N-methyl-D-aspartate receptor antago-nism by 3-N-substituted 2,3-benzodiazepines: Relationship to anticonvulsant activity
    • (c) Donevan, S. D.; Yamaguchi, S. I.; Rogawski, M. A. Non-N-methyl-D-aspartate Receptor Antago-nism by 3-N-Substituted 2,3-Benzodiazepines: Relationship to Anticonvulsant Activity. J. Pharmacol. Exp. Ther. 1994, 271, 25-29.
    • (1994) J. Pharmacol. Exp. Ther. , vol.271 , pp. 25-29
    • Donevan, S.D.1    Yamaguchi, S.I.2    Rogawski, M.A.3
  • 8
    • 0026623418 scopus 로고
    • Cerebroprotective effect of a non-N-methyl-d-aspartate antagonist, GYKI 52466, after focal ischemia in the rat
    • (a) Smith, S. E.; Meldrum, B. S. Cerebroprotective Effect of a Non-N-Methyl-d-Aspartate Antagonist, GYKI 52466, After Focal Ischemia in the Rat. Stroke 1992, 23, 861-864.
    • (1992) Stroke , vol.23 , pp. 861-864
    • Smith, S.E.1    Meldrum, B.S.2
  • 9
    • 0028351540 scopus 로고
    • Effect of the non-NMDA receptor antagonist GYKI 52466 on the microdialyzate and tissue concentrations of amino acids following transient forebrain ischemia
    • (b) Arvin, B.; Lekieffre, D.; Graham, J. L.; Moncada, C.; Chapman, A. G.; Meldrum, B. S. Effect of the Non-NMDA Receptor Antagonist GYKI 52466 on the Microdialyzate and Tissue Concentrations of Amino Acids Following Transient Forebrain Ischemia. J. Neurochem. 1994, 62, 1458-1467.
    • (1994) J. Neurochem. , vol.62 , pp. 1458-1467
    • Arvin, B.1    Lekieffre, D.2    Graham, J.L.3    Moncada, C.4    Chapman, A.G.5    Meldrum, B.S.6
  • 11
    • 0028836733 scopus 로고
    • Selective antagonism of AMPA receptors unmasks kainate receptor-mediate responses in hippocampal neurones
    • (b) Paternain A. V.; Morales, M.; Lerma, J. Selective Antagonism of AMPA Receptors Unmasks Kainate Receptor-Mediate Responses in Hippocampal Neurones. Neuron 1995, 14, 185-189.
    • (1995) Neuron , vol.14 , pp. 185-189
    • Paternain, A.V.1    Morales, M.2    Lerma, J.3
  • 12
    • 0027404879 scopus 로고
    • GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/kainate receptor responses
    • (a) Donevan, S. D.; Rogawski, M. A. GYKI 52466, a 2,3-Benzodiazepine, is a Highly Selective, Noncompetitive Antagonist of AMPA/Kainate Receptor Responses. Neuron 1993, 10, 51-59.
    • (1993) Neuron , vol.10 , pp. 51-59
    • Donevan, S.D.1    Rogawski, M.A.2
  • 13
    • 0027176541 scopus 로고
    • Therapeutic potential of excitatory amino acid antagonists: Channel blockers and 2,3-benzodiazepines
    • (b) Rogawski, M. A. Therapeutic Potential of Excitatory Amino Acid Antagonists: Channel Blockers and 2,3-Benzodiazepines. Trends Pharmacol. Sci. 1993, 14, 325-331.
    • (1993) Trends Pharmacol. Sci. , vol.14 , pp. 325-331
    • Rogawski, M.A.1
  • 17
    • 0033620391 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activity of new 2,3-benzodiazepines as AMPA receptor antagonists
    • (b) De Sarro, A.; De Sarro, G.; Gitto, R.; Grasso, S.; Micale, N.; Zappalà, M. Synthesis and Anticonvulsant Activity of New 2,3-Benzodiazepines as AMPA Receptor Antagonists. Farmaco 1999, 54, 179-189.
    • (1999) Farmaco , vol.54 , pp. 179-189
    • De Sarro, A.1    De Sarro, G.2    Gitto, R.3    Grasso, S.4    Micale, N.5    Zappalà, M.6
  • 18
    • 0032718907 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activity of novel and potent 2,3-benzodiazepine as noncompetitive AMPA/kainate receptor antagonists
    • (c) Grasso, S.; De Sarro, G, De Sarro, A.; Micale, N.; Zappalà, M.; Puja, G. Baraldi, M.; De Micheli, C. Synthesis and Anticonvulsant Activity of Novel and Potent 2,3-Benzodiazepine as Noncompetitive AMPA/Kainate Receptor Antagonists. J. Med. Chem. 1999, 42, 4414-21.
    • (1999) J. Med. Chem. , vol.42 , pp. 4414-4421
    • Grasso, S.1    De Sarro, G.2    De Sarro, A.3    Micale, N.4    Zappalà, M.5    Puja, G.6    Baraldi, M.7    De Micheli, C.8
  • 19
    • 0032474755 scopus 로고    scopus 로고
    • Synthesis of 7,8-(methylenedioxy)-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones as novel and potent noncompetitive AMPA receptor antagonists
    • Wang, Y.; Konkoy, C. S.; Ilvy, V. I.; Vanover, K. E.; Carter, R.; Weber, E.; Keana, J. F. W.; Woodward, R. M.; Cai, S. X. Synthesis of 7,8-(Methylenedioxy)-1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones as Novel and Potent Noncompetitive AMPA Receptor Antagonists. J. Med. Chem. 1998, 41, 2621-2625.
    • (1998) J. Med. Chem. , vol.41 , pp. 2621-2625
    • Wang, Y.1    Konkoy, C.S.2    Ilvy, V.I.3    Vanover, K.E.4    Carter, R.5    Weber, E.6    Keana, J.F.W.7    Woodward, R.M.8    Cai, S.X.9
  • 20
    • 0001218338 scopus 로고
    • Role of NMDA receptors in behavior and behavioral effects of drugs
    • Stone, T. W., Ed.; CRC Press: New York
    • (a) Witkin, J. M. Role of NMDA Receptors in Behavior and Behavioral Effects of Drugs. In CNS Neurotransmitters and Neuromodulators: Glutamate; Stone, T. W., Ed.; CRC Press: New York, 1995; pp 323-340.
    • (1995) CNS Neurotransmitters and Neuromodulators: Glutamate , pp. 323-340
    • Witkin, J.M.1
  • 21
    • 0012302192 scopus 로고
    • Behavioral effects of non-NMDA glutamate receptor antagonists
    • Stone, T. W., Ed.; CRC Press: New York
    • (b) Lalonde, R. Behavioral Effects of Non-NMDA Glutamate Receptor Antagonists. In CNS Neurotransmitters and Neuromodulators: Glutamate; Stone, T. W., Ed.; CRC Press: New York, 1995; pp 351-357.
    • (1995) CNS Neurotransmitters and Neuromodulators: Glutamate , pp. 351-357
    • Lalonde, R.1
  • 22
    • 0030034762 scopus 로고    scopus 로고
    • Substituted 1,2-dihydrophthalazines: Potent, selective, and noncompetitive inhibitors of the AMPA receptor
    • Pelletier, J. C.; Hesson, D. P.; Jones, K. A.; Costa, A. M. Substituted 1,2-Dihydrophthalazines: Potent, Selective, and Noncompetitive Inhibitors of the AMPA Receptor. J. Med. Chem. 1996, 39, 343-346.
    • (1996) J. Med. Chem. , vol.39 , pp. 343-346
    • Pelletier, J.C.1    Hesson, D.P.2    Jones, K.A.3    Costa, A.M.4
  • 23
    • 0021189693 scopus 로고
    • Evaluation of anticonvulsant drugs in DBA/2 mice with sound-induced seizures
    • (a) Chapman, A. G.; Croucher, M. J.; Meldrum, B. S. Evaluation of Anticonvulsant Drugs in DBA/2 Mice with Sound-Induced Seizures. Arzneim. Forsch. 1984, 34, 1261-1264.
    • (1984) Arzneim. Forsch. , vol.34 , pp. 1261-1264
    • Chapman, A.G.1    Croucher, M.J.2    Meldrum, B.S.3
  • 24
    • 0023742573 scopus 로고
    • Seizure susceptibility in DBA/2 and C57 mice: The effects of various convulsants
    • (b) Engstrom, F. L.; Woodbury, D. M. Seizure Susceptibility in DBA/2 and C57 Mice: the Effects of Various Convulsants. Epilepsia 1988, 29, 389-395.
    • (1988) Epilepsia , vol.29 , pp. 389-395
    • Engstrom, F.L.1    Woodbury, D.M.2
  • 25
    • 0025356607 scopus 로고
    • Allosteric potentiation of quisqualate receptors by nootropic drug aniracetam
    • Ito, I.; Tanabe, S.; Kohda, A.; Sugiyama, H. Allosteric Potentiation of Quisqualate Receptors by Nootropic Drug Aniracetam. J. Physiol. (London) 1990, 424, 533-543.
    • (1990) J. Physiol. (London) , vol.424 , pp. 533-543
    • Ito, I.1    Tanabe, S.2    Kohda, A.3    Sugiyama, H.4
  • 26
    • 0028296286 scopus 로고
    • Synthesis of 3-oxo-2,3-dihydroiso-quinolines from ethyl 2-acylphenylacetates and formamides
    • Venkov, A. P.; Ivanov, I. I. Synthesis of 3-Oxo-2,3-Dihydroiso-quinolines from Ethyl 2-Acylphenylacetates and Formamides. Synth. Commun. 1994, 24, 1145-1150.
    • (1994) Synth. Commun. , vol.24 , pp. 1145-1150
    • Venkov, A.P.1    Ivanov, I.I.2
  • 28
    • 0025852165 scopus 로고
    • Kinetic analysis of interactions between kainate and AMPA: Evidence for activation of a single receptor in mouse hippocampal neurons
    • (a) Patneau, D. K.; Mayer, M. L. Kinetic analysis of interactions between kainate and AMPA: evidence for activation of a single receptor in mouse hippocampal neurons. Neuron 1991, 6, 785-798.
    • (1991) Neuron , vol.6 , pp. 785-798
    • Patneau, D.K.1    Mayer, M.L.2
  • 29
    • 0028988215 scopus 로고
    • Differential antagonism of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-preferring and kainate-preferring receptors by 2,3-benzodiazepines
    • (b) Wilding, T. J.; Huettner, J. E. Differential antagonism of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-preferring and kainate-preferring receptors by 2,3-benzodiazepines. Mol. Pharmacol. 1995, 47, 582-587.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 582-587
    • Wilding, T.J.1    Huettner, J.E.2
  • 32
    • 0001477154 scopus 로고
    • A simple assessment of partition data for correlating structure and biological activity using thin-layer chromatography
    • (a) Boyce, C. B. C.; Milborrow, B. V. A Simple Assessment of Partition Data for Correlating Structure and Biological Activity Using Thin-Layer Chromatography. Nature 1965, 208, 537-539.
    • (1965) Nature , vol.208 , pp. 537-539
    • Boyce, C.B.C.1    Milborrow, B.V.2
  • 33
    • 0023791595 scopus 로고
    • Lipophilicity measurements of benzodiazepine-receptor ligands by reversed-phase liquid chromatography. Comparison between high-performance liquid and thin-layer chromatography
    • (b) Pietrogrande, M. C.; Borea, P. A.; Biagi, G. L. Lipophilicity Measurements of Benzodiazepine-Receptor Ligands by Reversed-Phase Liquid Chromatography. Comparison between High-Performance Liquid and Thin-Layer Chromatography. J. Chromatogr. 1988, 447, 404-409.
    • (1988) J. Chromatogr. , vol.447 , pp. 404-409
    • Pietrogrande, M.C.1    Borea, P.A.2    Biagi, G.L.3
  • 34
    • 0000390504 scopus 로고
    • Audiogenic seizures
    • Purpura, P., Penry, J. K., Tower, D., Woodbury, D. M., Walter, R., Eds.; Raven Press: New York
    • Collins, R. L. Audiogenic Seizures. In Experimental Models of Epilepsy; Purpura, P., Penry, J. K., Tower, D., Woodbury, D. M., Walter, R., Eds.; Raven Press: New York, 1972; pp 347-372.
    • (1972) Experimental Models of Epilepsy , pp. 347-372
    • Collins, R.L.1
  • 35
    • 0021259006 scopus 로고
    • Anticonvulsant actions of DS 103-282: Pharmacological studies in rodents and the baboon papio papio
    • De Sarro, G. B.; Croucher, M. J.; Meldrum, B. S. Anticonvulsant Actions of DS 103-282: Pharmacological Studies in Rodents and the Baboon Papio papio. Neuropharmacology 1984, 23, 526-530.
    • (1984) Neuropharmacology , vol.23 , pp. 526-530
    • De Sarro, G.B.1    Croucher, M.J.2    Meldrum, B.S.3
  • 37
    • 0001908712 scopus 로고
    • Experimental detection, quantification and evaluation of anticonvulsants
    • Woodbury, D. M., Penry, J. K., Pippenger, C. E., Eds.; Raven Press: New York
    • Swinyard, E. A.; Woodhead, J. M. Experimental Detection, Quantification and Evaluation of Anticonvulsants. In Epileptic Drugs; Woodbury, D. M., Penry, J. K., Pippenger, C. E., Eds.; Raven Press: New York, 1982; pp 111-126.
    • (1982) Epileptic Drugs , pp. 111-126
    • Swinyard, E.A.1    Woodhead, J.M.2
  • 38
    • 0028021395 scopus 로고
    • Excitatory amino acid neurotransmission through both NMDA and non-NMDA receptors is involved in the anticon-vulsant activity of felbamate in DBA/2 mice
    • De Sarro, G. B.; Ongini, E.; Bertorelli, R.; Aguglia, U.; De Sarro, A. Excitatory Amino Acid Neurotransmission through both NMDA and Non-NMDA Receptors is Involved in the Anticon-vulsant Activity of Felbamate in DBA/2 mice. Eur. J. Pharmacol. 1994, 262, 11-19.
    • (1994) Eur. J. Pharmacol. , vol.262 , pp. 11-19
    • De Sarro, G.B.1    Ongini, E.2    Bertorelli, R.3    Aguglia, U.4    De Sarro, A.5
  • 39
    • 0005982327 scopus 로고
    • Selective release of glutamate from cerebellar granule cells differentiating in culture
    • Gallo, V.; Ciotti, M. T.; Coletti, A.; Aloisi, F.; Levi, G. Selective Release of Glutamate from Cerebellar Granule Cells Differentiating in Culture. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 7919-7923.
    • (1982) Proc. Natl. Acad. Sci. U.S.A. , vol.79 , pp. 7919-7923
    • Gallo, V.1    Ciotti, M.T.2    Coletti, A.3    Aloisi, F.4    Levi, G.5
  • 40
    • 0019441262 scopus 로고
    • Improved patch clamp techniques for high-resolution current recording from cells and free-membrane patches
    • Hamil, O. P.; Marty, A.; Neher, E.; Sakmann, B.; Sigworth, F. J. Improved Patch Clamp Techniques for High-Resolution Current Recording from Cells and Free-membrane Patches. Pflugers Arch. 1981, 414, 85-100.
    • (1981) Pflugers Arch. , vol.414 , pp. 85-100
    • Hamil, O.P.1    Marty, A.2    Neher, E.3    Sakmann, B.4    Sigworth, F.J.5
  • 41
    • 0024348163 scopus 로고
    • Excitatory and inhibiting amino acids and peptide-induced responses in acutely isolated rat spinal horn neurons
    • Murase, K.; Ryu, P. D.; Randic, M. Excitatory and Inhibiting Amino Acids and Peptide-induced Responses in Acutely Isolated Rat Spinal Horn Neurons. Neurosci. Lett. 1989, 103, 56-63.
    • (1989) Neurosci. Lett. , vol.103 , pp. 56-63
    • Murase, K.1    Ryu, P.D.2    Randic, M.3
  • 42
    • 70449177837 scopus 로고
    • A note on a simple apparatus for detecting neurological deficit in rats and mice
    • Dunham, N. W.; Miya, T. S. A Note on a Simple Apparatus for Detecting Neurological Deficit in Rats and Mice. J. Am. Pharm. Assoc. 1957, 46, 208-209.
    • (1957) J. Am. Pharm. Assoc. , vol.46 , pp. 208-209
    • Dunham, N.W.1    Miya, T.S.2
  • 43
    • 84951384024 scopus 로고
    • A simplified method of evaluating dose-effect experiments
    • Litchfield, J.; Wilcoxon, F. A Simplified Method of Evaluating Dose-Effect Experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
    • (1949) J. Pharmacol. Exp. Ther. , vol.96 , pp. 99-113
    • Litchfield, J.1    Wilcoxon, F.2


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