메뉴 건너뛰기




Volumn 39, Issue 2, 1996, Pages 407-423

Syntheses and conformational analyses of glutamate analogs: 2-(2-carboxy-3-substituted-cyclopropyl)glycines as useful probes for excitatory amino acid receptors

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 CARBOXYCYCLOPROPYL)GLYCINE DERIVATIVE; 2 [2 CARBOXY 3 (METHOXYMETHYL)CYCLOPROPYL]GLYCINE DERIVATIVE; AMPA RECEPTOR; CYCLOPROPANE DERIVATIVE; EXCITATORY AMINO ACID RECEPTOR; GLUTAMIC ACID DERIVATIVE; KAINIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

EID: 0030045674     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9502908     Document Type: Article
Times cited : (132)

References (104)
  • 1
    • 0024596865 scopus 로고
    • The excitatory amino acid receptors: Their classes, pharmacology and distinct properties in the function of the central nervous system
    • (a) Monaghan, D. T.; Bridges, R. J.; Cotman, C. W. The excitatory amino acid receptors: their classes, pharmacology and distinct properties in the function of the central nervous system. Annu. Rev. Pharmacol. Toxicol. 1989, 29, 365-402.
    • (1989) Annu. Rev. Pharmacol. Toxicol. , vol.29 , pp. 365-402
    • Monaghan, D.T.1    Bridges, R.J.2    Cotman, C.W.3
  • 2
    • 0025191432 scopus 로고
    • Structure, activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists
    • (b) Watkins, J. C.; Krogsgaard-Larsen, P.; Honorè, T. Structure, activity relationships in the development of excitatory amino acid receptor agonists and competitive antagonists. Trends Pharmacol. Sci. 1990, 11, 25-53.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 25-53
    • Watkins, J.C.1    Krogsgaard-Larsen, P.2    Honorè, T.3
  • 3
    • 0023180067 scopus 로고
    • NMDA receptor-their role in long-term potentiation
    • (a) Collingridge, G. L.; Bliss, T. V. P. NMDA receptor-their role in long-term potentiation. Trends Neurosci. 1987, 10, 288-293.
    • (1987) Trends Neurosci. , vol.10 , pp. 288-293
    • Collingridge, G.L.1    Bliss, T.V.P.2
  • 4
    • 0026089090 scopus 로고
    • Mechanisms underlying long-term potentiation of synaptic transmission
    • (b) Madison, D. V.; Malenka, R. C.; Nicoll, R. A. Mechanisms underlying long-term potentiation of synaptic transmission. Annu. Rev. Neurosci. 1991, 14, 379-397.
    • (1991) Annu. Rev. Neurosci. , vol.14 , pp. 379-397
    • Madison, D.V.1    Malenka, R.C.2    Nicoll, R.A.3
  • 5
    • 0027967167 scopus 로고
    • Induction of an olfactory memory by the activation of a metabotropic glutamate receptor
    • (c) Kaba, H.; Hayashi, Y.; Higuchi, T.; Nakanishi, S. Induction of an olfactory memory by the activation of a metabotropic glutamate receptor. Science 1994, 265, 262-264.
    • (1994) Science , vol.265 , pp. 262-264
    • Kaba, H.1    Hayashi, Y.2    Higuchi, T.3    Nakanishi, S.4
  • 6
    • 0025063609 scopus 로고
    • Excitatory amino acid neurotoxicity and neurodegenerative disease
    • (a) Meldrum, B.; Garthwaite, J. Excitatory amino acid neurotoxicity and neurodegenerative disease. Trends Pharmacol. Sci. 1990, 11, 379-387.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 379-387
    • Meldrum, B.1    Garthwaite, J.2
  • 7
    • 0025304789 scopus 로고
    • Excitotoxic amino acids and neuropsychiatrie disorders
    • (b) Olney, J. W. Excitotoxic amino acids and neuropsychiatrie disorders. Annu. Rev. Pharmacol. Toxicol. 1990, 30, 47-71.
    • (1990) Annu. Rev. Pharmacol. Toxicol. , vol.30 , pp. 47-71
    • Olney, J.W.1
  • 8
    • 0025265926 scopus 로고
    • The role of glutamate neurotoxicity in hypoxic-ischemic neuronal death
    • (c) Choi, D. W.; Rothman, S. M. The role of glutamate neurotoxicity in hypoxic-ischemic neuronal death. Annu. Rev. Neurosci. 1990, 13, 171-182.
    • (1990) Annu. Rev. Neurosci. , vol.13 , pp. 171-182
    • Choi, D.W.1    Rothman, S.M.2
  • 9
    • 0022370635 scopus 로고
    • Glutamate stimulates inositol phosphate formation in striatal neurons
    • (a) Sladeczek, F.; Pin, J. P.; Recasens, M.; Bockaert, J.; Weiss, S. Glutamate stimulates inositol phosphate formation in striatal neurons. Nature 1985, 317, 717-719.
    • (1985) Nature , vol.317 , pp. 717-719
    • Sladeczek, F.1    Pin, J.P.2    Recasens, M.3    Bockaert, J.4    Weiss, S.5
  • 10
    • 0024335555 scopus 로고
    • Trans-ACPD, a selective agonist of phosphoinositide-coupled excitatory amino acid receptors
    • (b) Palmer, E.; Monaghan, D. T.; Cotman, C. W. Trans-ACPD, a selective agonist of phosphoinositide-coupled excitatory amino acid receptors. Eur. J. Pharmacol. 1989, 166, 585-597.
    • (1989) Eur. J. Pharmacol. , vol.166 , pp. 585-597
    • Palmer, E.1    Monaghan, D.T.2    Cotman, C.W.3
  • 11
    • 0026593238 scopus 로고
    • A family of metabotropic glutamate receptors
    • mGluRs of rat brain have been cloned and subdivided into mGluR1-7. It has been reported that mGluR1 and -5 were coupled with a stimulation of an intracellular IPs hydrolysis and mGluR2-4, -6, and -7 were negatively coupled to adenyl cyclase activity. (a) Tanabe, Y.; Masu, M.; Ishii, T.; Shigemoto, R.; Nakanishi, S. A family of metabotropic glutamate receptors. Neuron 1992, 8, 169-179. (b) Hayashi, Y.; Momiyama, A.; Takahashi, T.; Ohishi, H.; Ogawa-Meguro, R.; Shigemoto, R.; Mizuno, N.; Nakanishi, S. Role of a metabotropic glutamate receptor in synaptic modulation in the accessory olfactory bulb. Nature 1993, 366, 687-688.
    • (1992) Neuron , vol.8 , pp. 169-179
    • Tanabe, Y.1    Masu, M.2    Ishii, T.3    Shigemoto, R.4    Nakanishi, S.5
  • 12
    • 0027732539 scopus 로고
    • Role of a metabotropic glutamate receptor in synaptic modulation in the accessory olfactory bulb
    • mGluRs of rat brain have been cloned and subdivided into mGluR1-7. It has been reported that mGluR1 and -5 were coupled with a stimulation of an intracellular IPs hydrolysis and mGluR2-4, -6, and -7 were negatively coupled to adenyl cyclase activity. (a) Tanabe, Y.; Masu, M.; Ishii, T.; Shigemoto, R.; Nakanishi, S. A family of metabotropic glutamate receptors. Neuron 1992, 8, 169-179. (b) Hayashi, Y.; Momiyama, A.; Takahashi, T.; Ohishi, H.; Ogawa-Meguro, R.; Shigemoto, R.; Mizuno, N.; Nakanishi, S. Role of a metabotropic glutamate receptor in synaptic modulation in the accessory olfactory bulb. Nature 1993, 366, 687-688.
    • (1993) Nature , vol.366 , pp. 687-688
    • Hayashi, Y.1    Momiyama, A.2    Takahashi, T.3    Ohishi, H.4    Ogawa-Meguro, R.5    Shigemoto, R.6    Mizuno, N.7    Nakanishi, S.8
  • 13
    • 0026437728 scopus 로고
    • Molecular diversity of glutamate receptors and implications for brain function
    • references cited therein
    • Nakanishi, S. Molecular diversity of glutamate receptors and implications for brain function. Science 1992, 258, 597-603 and references cited therein.
    • (1992) Science , vol.258 , pp. 597-603
    • Nakanishi, S.1
  • 14
    • 0004195588 scopus 로고
    • Actions of amino-acids on the isolated hemisected spinal cord of the toad
    • (a) For the 3-point binding hypothesis, see: Curtis, D. R.; Phillis, J. W.; Watkins, J. C. Actions of amino-acids on the isolated hemisected spinal cord of the toad. Br. J. Pharmacol. 1961, 16, 262-283.
    • (1961) Br. J. Pharmacol. , vol.16 , pp. 262-283
    • Curtis, D.R.1    Phillis, J.W.2    Watkins, J.C.3
  • 15
    • 0020401599 scopus 로고
    • Conformational aspects of the actions of some piperidine dicarboxylic acids at excitatory amino acid receptors in the mammalian and amphibian spinal cord
    • (b) For a proposed conformational requirement of NMDA receptors, see: Davies, J.; Evans, R. H.; Francis, A. A.; Jones, D.; Smith, A. S.; Watkins, J. C. Conformational aspects of the actions of some piperidine dicarboxylic acids at excitatory amino acid receptors in the mammalian and amphibian spinal cord. Neurochem. Res. 1982, 7, 1119-1133.
    • (1982) Neurochem. Res. , vol.7 , pp. 1119-1133
    • Davies, J.1    Evans, R.H.2    Francis, A.A.3    Jones, D.4    Smith, A.S.5    Watkins, J.C.6
  • 16
    • 0023875531 scopus 로고
    • Synthesis of trans- and cis-α-(carboxycyclopropyl)glycines. Novel neuroinhibitory amino acids as L-glutamate analogue
    • (a) Yamanoi, K.; Ohfune, Y.; Watanabe, K.; Li, P.-N.; Takeuchi, H. Synthesis of trans- and cis-α-(carboxycyclopropyl)glycines. Novel neuroinhibitory amino acids as L-glutamate analogue. Tetrahedron Lett. 1988, 29, 1181-1184.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 1181-1184
    • Yamanoi, K.1    Ohfune, Y.2    Watanabe, K.3    Li, P.-N.4    Takeuchi, H.5
  • 17
    • 0025797354 scopus 로고
    • Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogues
    • (b) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogues. J. Org. Chem. 1991, 56, 4167-4176.
    • (1991) J. Org. Chem. , vol.56 , pp. 4167-4176
    • Shimamoto, K.1    Ishida, M.2    Shinozaki, H.3    Ohfune, Y.4
  • 18
    • 85033857607 scopus 로고    scopus 로고
    • CCGs are now commercially available from Tocris Cookson Ltd., Bristol, U.K.
    • (c) CCGs are now commercially available from Tocris Cookson Ltd., Bristol, U.K.
  • 19
    • 0024495582 scopus 로고
    • A conformationally restricted analogue of L-glutamate, the (2S,3R,4S) isomer of L-α-(carboxycyclopropyl)glycine, activates the NMDA-type receptor more markedly than NMDA in the isolated rat spinal cord
    • (a) Shinozaki, H.; Ishida, M.; Shimamoto, K.; Ohfune, Y. A conformationally restricted analogue of L-glutamate, the (2S,3R,4S) isomer of L-α-(carboxycyclopropyl)glycine, activates the NMDA-type receptor more markedly than NMDA in the isolated rat spinal cord. Brain Res. 1989, 480, 355-359.
    • (1989) Brain Res. , vol.480 , pp. 355-359
    • Shinozaki, H.1    Ishida, M.2    Shimamoto, K.3    Ohfune, Y.4
  • 20
    • 0024843541 scopus 로고
    • Potent NMDA-like actions and potentiation of glutamate receptors by conformational variants of a glutamate analogue in the rat spinal cord
    • (b) Shinozaki, H.; Ishida, M.; Shimamoto, K.; Ohfune, Y. Potent NMDA-like actions and potentiation of glutamate receptors by conformational variants of a glutamate analogue in the rat spinal cord. Br. J. Pharmacol. 1989, 98, 1213-1224.
    • (1989) Br. J. Pharmacol. , vol.98 , pp. 1213-1224
    • Shinozaki, H.1    Ishida, M.2    Shimamoto, K.3    Ohfune, Y.4
  • 21
    • 0026331028 scopus 로고
    • 2+ concentration induced by (2S,3R,4S)-2-(carboxycyclopropyl)glycine, a new potent agonist, in cultured rat hippocampal neurones
    • 2+ concentration induced by (2S,3R,4S)-2-(carboxycyclopropyl)glycine, a new potent agonist, in cultured rat hippocampal neurones. Brain Res. 1991, 567, 342-345.
    • (1991) Brain Res. , vol.567 , pp. 342-345
    • Kudo, Y.1    Akita, K.2    Ishida, M.3    Shinozaki, H.4
  • 23
    • 0027441565 scopus 로고
    • 3H]glutamate transport activity: Pharmacologic specificity and regulation by sodium and potassium
    • 3H]glutamate transport activity: pharmacologic specificity and regulation by sodium and potassium. J. Neurochem. 1993, 60, 167-179.
    • (1993) J. Neurochem. , vol.60 , pp. 167-179
    • Robinson, M.B.1    Sinor, J.D.2    Dowd, L.A.3    Kerwin Jr., J.F.4
  • 24
    • 0027216795 scopus 로고
    • (2S,3S,4R)-2-(Carboxycyclopropyl)glycine, a potent and competitive inhibitor of both glial and neuronal uptake of glutamate
    • (f) Nakamura, Y.; Kataoka, K.; Ishida, M.; Shinozaki, H. (2S,3S,4R)-2-(Carboxycyclopropyl)glycine, a potent and competitive inhibitor of both glial and neuronal uptake of glutamate. Neuropharmacology 1993, 32, 833-837.
    • (1993) Neuropharmacology , vol.32 , pp. 833-837
    • Nakamura, Y.1    Kataoka, K.2    Ishida, M.3    Shinozaki, H.4
  • 25
    • 0025079146 scopus 로고
    • (2S,3S,4S)-α-(Carboxycyclopropyl)glycine is a novel agonist of metabotropic glutamate receptors
    • (a) Nakagawa, Y.; Saitoh, K.; Ishihara, T.; Ishida, M.; Shinozaki, H. (2S,3S,4S)-α-(Carboxycyclopropyl)glycine is a novel agonist of metabotropic glutamate receptors. Eur. J. Pharmacol. 1990, 184, 205-206.
    • (1990) Eur. J. Pharmacol. , vol.184 , pp. 205-206
    • Nakagawa, Y.1    Saitoh, K.2    Ishihara, T.3    Ishida, M.4    Shinozaki, H.5
  • 26
    • 0025696335 scopus 로고
    • A potent metabotropic glutamate receptor agonist: Electrophysiological actions of a conformationally restricted glutamate analogue in the rat spinal cord and Xenopus oocytes
    • (b) Ishida, M.; Akagi, H.; Shimamoto, K.; Ohfune, Y.; Shinozaki, H. A potent metabotropic glutamate receptor agonist: electrophysiological actions of a conformationally restricted glutamate analogue in the rat spinal cord and Xenopus oocytes. Brain Res. 1990, 537, 311-314.
    • (1990) Brain Res. , vol.537 , pp. 311-314
    • Ishida, M.1    Akagi, H.2    Shimamoto, K.3    Ohfune, Y.4    Shinozaki, H.5
  • 27
    • 0026756866 scopus 로고
    • Agonist analysis of 2-(carboxycyclopropyl)glycine isomers for cloned metabotropic glutamate receptor subtypes expressed in Chinese hamster ovary cells
    • (c) Hayashi, Y.; Tanabe, Y.; Aramori, I.; Masu, M.; Shimamoto, K.; Ohfune, Y.; Nakanishi, S. Agonist analysis of 2-(carboxycyclopropyl)glycine isomers for cloned metabotropic glutamate receptor subtypes expressed in Chinese hamster ovary cells. Br. J. Pharmacol. 1992, 107, 539-543.
    • (1992) Br. J. Pharmacol. , vol.107 , pp. 539-543
    • Hayashi, Y.1    Tanabe, Y.2    Aramori, I.3    Masu, M.4    Shimamoto, K.5    Ohfune, Y.6    Nakanishi, S.7
  • 28
    • 0027209890 scopus 로고
    • A novel metabotropic glutamate receptor agonist: Marked depression of monosynaptic excitation in the newborn rat isolated spinal cord
    • (d) Ishida, M.; Saitoh, T.; Shimamoto, K.; Ohfune, Y.; Shinozaki, H. A novel metabotropic glutamate receptor agonist: marked depression of monosynaptic excitation in the newborn rat isolated spinal cord. Br. J. Pharmacol. 1993, 109, 1169-1177.
    • (1993) Br. J. Pharmacol. , vol.109 , pp. 1169-1177
    • Ishida, M.1    Saitoh, T.2    Shimamoto, K.3    Ohfune, Y.4    Shinozaki, H.5
  • 29
    • 0010457889 scopus 로고
    • L-2-(Carboxycyclopropyl)glycines: Conformationally constrained L-glutamate analogues
    • Kozikowski, A. P., Ed.; Raven Press: New York
    • Ohfune, Y.; Shinozaki, H. L-2-(Carboxycyclopropyl)glycines: conformationally constrained L-glutamate analogues. In Drug Design for Neuroscience; Kozikowski, A. P., Ed.; Raven Press: New York, 1993; pp 261-283.
    • (1993) Drug Design for Neuroscience , pp. 261-283
    • Ohfune, Y.1    Shinozaki, H.2
  • 30
    • 0025376117 scopus 로고
    • Syntheses of 3′-substituted-2-(carboxycyclopropyl)glycines via intramolecular cyclopropanation. The folded form of L-glutamate activates the non-NMDA receptor subtype
    • Parts of the synthesis and pharmacological profile of MCGs were published in preliminary reports. (a) Shimamoto, K.; Ohfune, Y. Syntheses of 3′-substituted-2-(carboxycyclopropyl)glycines via intramolecular cyclopropanation. The folded form of L-glutamate activates the non-NMDA receptor subtype. Tetrahedron Lett. 1990, 31, 4049-4052. (b) Shimamoto, K.; Ohfune, Y. Inversion of cis-substituted α-cyclopropyl acyl anion. Stereoselective entry to the synthesis of a potent metabotropic glutamate agonist, (2S,1′S,2′S)-2-(carboxycyclopropyl)glycine (L-CCG-I), and its 3′-substituted analogues. Synlett 1993, 919-920.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4049-4052
    • Shimamoto, K.1    Ohfune, Y.2
  • 31
    • 85064549206 scopus 로고
    • Inversion of cis-substituted α-cyclopropyl acyl anion. Stereoselective entry to the synthesis of a potent metabotropic glutamate agonist, (2S,1′S,2′S)-2-(carboxycyclopropyl)glycine (L-CCG-I), and its 3′-substituted analogues
    • Parts of the synthesis and pharmacological profile of MCGs were published in preliminary reports. (a) Shimamoto, K.; Ohfune, Y. Syntheses of 3′-substituted-2-(carboxycyclopropyl)glycines via intramolecular cyclopropanation. The folded form of L-glutamate activates the non-NMDA receptor subtype. Tetrahedron Lett. 1990, 31, 4049-4052. (b) Shimamoto, K.; Ohfune, Y. Inversion of cis-substituted α-cyclopropyl acyl anion. Stereoselective entry to the synthesis of a potent metabotropic glutamate agonist, (2S,1′S,2′S)-2-(carboxycyclopropyl)glycine (L-CCG-I), and its 3′-substituted analogues. Synlett 1993, 919-920.
    • (1993) Synlett , pp. 919-920
    • Shimamoto, K.1    Ohfune, Y.2
  • 32
    • 0003161893 scopus 로고
    • 1,1-Dimethylethyl (S)- or (R)-4-formyl-2,2-dimethyl-3-oxazolidine carboxylate: A useful serinal derivative
    • (a) Garner, P.; Park, J. M. 1,1-Dimethylethyl (S)- or (R)-4-formyl-2,2-dimethyl-3-oxazolidine carboxylate: a useful serinal derivative. Org. Synth. 1991, 70, 18-28.
    • (1991) Org. Synth. , vol.70 , pp. 18-28
    • Garner, P.1    Park, J.M.2
  • 33
    • 33845282544 scopus 로고
    • The synthesis and configurational stability of differentially protected β-hydroxy-α-amino aldehyde
    • (b) Garner, P.; Park, J. M. The synthesis and configurational stability of differentially protected β-hydroxy-α-amino aldehyde. J. Org. Chem. 1987, 52, 2361-2364.
    • (1987) J. Org. Chem. , vol.52 , pp. 2361-2364
    • Garner, P.1    Park, J.M.2
  • 34
    • 0026567703 scopus 로고
    • Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid
    • Sakai, N.; Ohfune, Y. Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid. J. Am. Chem. Soc. 1992, 114, 998-1010.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 998-1010
    • Sakai, N.1    Ohfune, Y.2
  • 35
    • 0000703358 scopus 로고
    • Selective transformation of N-t-butoxycarbonyl group into N-alkoxycarbonyl group via N-carboxylate ion equivalent
    • (a) Sakaitani, M.; Ohfune, Y. Selective transformation of N-t-butoxycarbonyl group into N-alkoxycarbonyl group via N-carboxylate ion equivalent. Tetrahedron Lett. 1985, 26, 5543-5546.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5543-5546
    • Sakaitani, M.1    Ohfune, Y.2
  • 36
    • 0025356803 scopus 로고
    • Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protective groups via tert-butyldimethylsilyl carbamates
    • (b) Sakaitani, M.; Ohfune, Y. Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protective groups via tert-butyldimethylsilyl carbamates. J. Org. Chem. 1990, 55, 870-876.
    • (1990) J. Org. Chem. , vol.55 , pp. 870-876
    • Sakaitani, M.1    Ohfune, Y.2
  • 37
    • 85033864593 scopus 로고    scopus 로고
    • note
    • The exclusive exo cycloaddition might be attributed to its putative transition state conformation 4 which is sterically more favorable than that of the endo transition state.
  • 38
    • 85033862260 scopus 로고    scopus 로고
    • note
    • 2 was purified prior to use (see the Experimental Section). We thank Professor M. Mandai, Okayama University of Science, for informing us of this purification procedure.
  • 39
    • 85033860409 scopus 로고    scopus 로고
    • note
    • Methylation of the primary alcohol using NaH/MeI was not satisfactory since a considerable amount of N-methylated byproduct was also obtained.
  • 40
    • 0027534340 scopus 로고
    • Synthesis of L-2-(2,3-dicarboxycyclopropyl)glycines. Novel conformationally restricted glutamate analogues
    • Ohfune, Y.; Shimamoto, K.; Ishida, M.; Shinozaki, H. Synthesis of L-2-(2,3-dicarboxycyclopropyl)glycines. Novel conformationally restricted glutamate analogues. Bioorg. Med. Chem. Lett. 1993, 3, 15-18.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 15-18
    • Ohfune, Y.1    Shimamoto, K.2    Ishida, M.3    Shinozaki, H.4
  • 41
    • 0024359305 scopus 로고    scopus 로고
    • New routes to the synthesis of cis-α-(carboxycyclopropyl)glycines from L-glutamic acid. Conformationally constrained analogues of the excitatory neurotransmitter L-glutamic acid
    • Prepared from (2S,1′S,2′R)-n-(tert-butoxycarbonyl)-2-[(ethoxycarbonyl)cyclopropyl] glycinol. (a) Shimamoto, K.; Ohfune, Y. New routes to the synthesis of cis-α-(carboxycyclopropyl)glycines from L-glutamic acid. Conformationally constrained analogues of the excitatory neurotransmitter L-glutamic acid. Tetrahedron Lett. 1980, 30, 3803-3894. (b) See ref 8b.
    • (1980) Tetrahedron Lett. , vol.30 , pp. 3803-3894
    • Shimamoto, K.1    Ohfune, Y.2
  • 42
    • 0024359305 scopus 로고    scopus 로고
    • See ref 8b
    • Prepared from (2S,1′S,2′R)-n-(tert-butoxycarbonyl)-2-[(ethoxycarbonyl)cyclopropyl] glycinol. (a) Shimamoto, K.; Ohfune, Y. New routes to the synthesis of cis-α-(carboxycyclopropyl)glycines from L-glutamic acid. Conformationally constrained analogues of the excitatory neurotransmitter L-glutamic acid. Tetrahedron Lett. 1980, 30, 3803-3894. (b) See ref 8b.
  • 43
    • 85033840531 scopus 로고    scopus 로고
    • note
    • 2.
  • 44
    • 0344887064 scopus 로고
    • Equilibrium acidities in dimethyl sulfoxide solution
    • Bordwell, F. G. Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 1988, 21, 456-463.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 456-463
    • Bordwell, F.G.1
  • 45
    • 33845554518 scopus 로고
    • High diastereoselection in the alkylation of siloxy-substituted methyl cyclopropanecarboxylates: Consequence of a pyramidal ester enolate anion?
    • Pyramidal α-cyclopropyl ester anion has been reported. (a) Reissig, H.-U.; Böhm, I. High diastereoselection in the alkylation of siloxy-substituted methyl cyclopropanecarboxylates: consequence of a pyramidal ester enolate anion? J. Am. Chem. Soc. 1982, 104, 1735-1737. (b) Reissig, H.-U. Donor-acceptor-substituted cyclopropanes: versatile building blocks in organic synthesis. Topics in Current Chemistry; Springer-Verlag: Berlin, 1988; Vol. 144, pp 75-135.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1735-1737
    • Reissig, H.-U.1    Böhm, I.2
  • 46
    • 33845554518 scopus 로고
    • Donor-acceptor-substituted cyclopropanes: Versatile building blocks in organic synthesis
    • Springer-Verlag: Berlin
    • Pyramidal α-cyclopropyl ester anion has been reported. (a) Reissig, H.-U.; Böhm, I. High diastereoselection in the alkylation of siloxy-substituted methyl cyclopropanecarboxylates: consequence of a pyramidal ester enolate anion? J. Am. Chem. Soc. 1982, 104, 1735-1737. (b) Reissig, H.-U. Donor-acceptor-substituted cyclopropanes: versatile building blocks in organic synthesis. Topics in Current Chemistry; Springer-Verlag: Berlin, 1988; Vol. 144, pp 75-135.
    • (1988) Topics in Current Chemistry , vol.144 , pp. 75-135
    • Reissig, H.-U.1
  • 47
    • 33947470356 scopus 로고
    • Cyclopropanes: The cyclopropyl carbanion
    • (a) Walborsky, H. M.; Hornyak, F. M. Cyclopropanes: the cyclopropyl carbanion. J. Am. Chem. Soc. 1955, 77, 6026-6029.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 6026-6029
    • Walborsky, H.M.1    Hornyak, F.M.2
  • 48
    • 0001505175 scopus 로고
    • Cyclopropanes. XXV. The cyclopropyl anion
    • (b) Walborsky, H. M.; Motes, J. M. Cyclopropanes. XXV. The cyclopropyl anion. J. Am. Chem. Soc. 1970, 92, 2445-2450.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 2445-2450
    • Walborsky, H.M.1    Motes, J.M.2
  • 49
    • 0038368991 scopus 로고
    • The chemistry of small ring compounds-XIV. Acidity of cyclopropanes with electron-withdrawing substituents
    • (c) van Wijnen, Th.; Steinberg, H.; de Boer, Th. J. The chemistry of small ring compounds-XIV. Acidity of cyclopropanes with electron-withdrawing substituents. Tetrahedron 1972, 28, 5423-5432.
    • (1972) Tetrahedron , vol.28 , pp. 5423-5432
    • Van Wijnen, Th.1    Steinberg, H.2    De Boer, Th.J.3
  • 50
    • 0025278995 scopus 로고
    • Stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes as novel dipeptide isosteres
    • Martin, S. F.; Austin, R. E.; Oalmann, C. J. Stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes as novel dipeptide isosteres. Tetrahedron Lett 1990, 31, 4731-4734.
    • (1990) Tetrahedron Lett , vol.31 , pp. 4731-4734
    • Martin, S.F.1    Austin, R.E.2    Oalmann, C.J.3
  • 51
    • 0025811150 scopus 로고
    • Changes in preference for receptor subtypes of configurational variants of a glutamate analog: Conversion from the NMDA-type to the non-NMDA type
    • Ishida, M.; Ohfune, Y.; Shimada, Y.; Shimamoto, K.; Shinozaki, H. Changes in preference for receptor subtypes of configurational variants of a glutamate analog: conversion from the NMDA-type to the non-NMDA type. Brain Res. 1991, 550, 152-156.
    • (1991) Brain Res. , vol.550 , pp. 152-156
    • Ishida, M.1    Ohfune, Y.2    Shimada, Y.3    Shimamoto, K.4    Shinozaki, H.5
  • 52
    • 0029102084 scopus 로고
    • Novel agonists for metabotropic receptors: Trans-and cis-2-(2-carboxy-3-methoxymethylcyclopropyl)glycine (trans-and cis-MCG-I)
    • Ishida, M.; Saitoh, T.; Tsuji, K.; Nakamura, Y.; Kataoka, K.; Shinozaki, H. Novel agonists for metabotropic receptors: trans-and cis-2-(2-carboxy-3-methoxymethylcyclopropyl)glycine (trans-and cis-MCG-I). Neuropharmacology 1995, 34, 821-827.
    • (1995) Neuropharmacology , vol.34 , pp. 821-827
    • Ishida, M.1    Saitoh, T.2    Tsuji, K.3    Nakamura, Y.4    Kataoka, K.5    Shinozaki, H.6
  • 53
    • 0028169097 scopus 로고
    • A novel metabotropic receptor agonist: (2S,1′S,2′R,3′R)-2-(2-carboxy-3-methoxymethylcyclopropyl) glycine (cis-MCG-I)
    • Ishida, M.; Saitoh, T.; Nakamura, Y.; Kataoka, K.; Shinozaki, H. A novel metabotropic receptor agonist: (2S,1′S,2′R,3′R)-2-(2-carboxy-3-methoxymethylcyclopropyl) glycine (cis-MCG-I). Eur. J. Pharmacol., Mol. Pharmacol. Sect. 1994, 268, 267-270.
    • (1994) Eur. J. Pharmacol., Mol. Pharmacol. Sect. , vol.268 , pp. 267-270
    • Ishida, M.1    Saitoh, T.2    Nakamura, Y.3    Kataoka, K.4    Shinozaki, H.5
  • 54
    • 0011335428 scopus 로고
    • Actions of the four isomers of 1-aminocyclopentane-1,3-dicarboxylate (ACPD) in the hemisected isolated spinal cord of the neonatal rat
    • For presynaptic inhibition, see: (a) Sunter, D. C.; Edgar, G. E.; Pook, P. C.; Howard, J. A. K.; Udvarhelyi, P. M.; Watkins, J. C. Actions of the four isomers of 1-aminocyclopentane-1,3-dicarboxylate (ACPD) in the hemisected isolated spinal cord of the neonatal rat. Br. J. Pharmacol. 1991, 104, 377P. (b) Cotman, C. W.; Flatman, J. A.; Ganong, A. H.; Perkius, M. N. Effects of excitatory amino acid antagonists on evoked and spontaneous excitatory potentials in guinea-pig hippocampus. J. Physiol. 1986, 378, 403-415.
    • (1991) Br. J. Pharmacol. , vol.104
    • Sunter, D.C.1    Edgar, G.E.2    Pook, P.C.3    Howard, J.A.K.4    Udvarhelyi, P.M.5    Watkins, J.C.6
  • 55
    • 0022558284 scopus 로고
    • Effects of excitatory amino acid antagonists on evoked and spontaneous excitatory potentials in guinea-pig hippocampus
    • For presynaptic inhibition, see: (a) Sunter, D. C.; Edgar, G. E.; Pook, P. C.; Howard, J. A. K.; Udvarhelyi, P. M.; Watkins, J. C. Actions of the four isomers of 1-aminocyclopentane-1,3-dicarboxylate (ACPD) in the hemisected isolated spinal cord of the neonatal rat. Br. J. Pharmacol. 1991, 104, 377P. (b) Cotman, C. W.; Flatman, J. A.; Ganong, A. H.; Perkius, M. N. Effects of excitatory amino acid antagonists on evoked and spontaneous excitatory potentials in guinea-pig hippocampus. J. Physiol. 1986, 378, 403-415.
    • (1986) J. Physiol. , vol.378 , pp. 403-415
    • Cotman, C.W.1    Flatman, J.A.2    Ganong, A.H.3    Perkius, M.N.4
  • 56
    • 0003601534 scopus 로고
    • Merck & Co., Inc.: Rathway, NJ
    • 3 = 9.67. Merck Index, 8th ed.; Merck & Co., Inc.: Rathway, NJ, 1989; p 4363.
    • (1989) Merck Index, 8th Ed. , pp. 4363
  • 57
    • 0000506574 scopus 로고
    • Studies on the active components of Digenea simplex Ag, and related compounds, I. Studies on the structure of kainic acid (1)
    • a values of kainic acid, see: Ueno, Y.; Nawa, H.; Ueyanagi, J.; Morimoto, H.; Nakamori, R.; Matsuoka, T. Studies on the active components of Digenea simplex Ag, and related compounds, I. Studies on the structure of kainic acid (1). Yakugaku Zasshi 1955, 75, 807-811.
    • (1955) Yakugaku Zasshi , vol.75 , pp. 807-811
    • Ueno, Y.1    Nawa, H.2    Ueyanagi, J.3    Morimoto, H.4    Nakamori, R.5    Matsuoka, T.6
  • 58
    • 0010974289 scopus 로고
    • Nuclear magnetic resonance spectra of amino acids and their derivatives
    • Barret, G. C., Ed.; Chapman and Hall: New York
    • Barret, G. C.; Davies, J. S. Nuclear magnetic resonance spectra of amino acids and their derivatives. In Chemistry and biochemistry of the amino acids; Barret, G. C., Ed.; Chapman and Hall: New York, 1985; pp 525-544.
    • (1985) Chemistry and Biochemistry of the Amino Acids , pp. 525-544
    • Barret, G.C.1    Davies, J.S.2
  • 59
    • 85033859092 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 60
    • 85033846948 scopus 로고    scopus 로고
    • note
    • The C-2H of CCG-IV was observed as a broad signal at pH 9-11 where slow exchange of the nonprotonated and the protonated amino group might affect the broadening of the signal at C-2H.
  • 61
    • 85033867094 scopus 로고    scopus 로고
    • note
    • 2H-1′H values of trans-MCG-III and -IV (pH > 8-0) and cis-MCG-IV (pH > 9) could not be obtained because of the broadening signals of both 2H and 1′H.
  • 63
    • 85033845159 scopus 로고    scopus 로고
    • note
    • The rotation of both the carboxylates of CCGs did not affect the minimization.
  • 64
    • 85033853931 scopus 로고    scopus 로고
    • note
    • Calculations of cis-MCG-I and -IV were performed by rotating the C2-C1′ bond and the two bonds of the C3′ methoxymethyl group (in 60° increments) and provided 32 and 23 minimized structures, respectively. Among them, the existence ratio of the H-C2-C1′-H antiperiplanar type conformers were 96.6% for cis-MCG-I and 99.3% for cis-MCG-IV. These results were in good agreement with those of Me-substituted CCGs.
  • 65
    • 85033856692 scopus 로고    scopus 로고
    • note
    • We thank Dr. N. Hamanaka, Director, Minase Research Institute of Ono Pharmaceutical Co. Ltd., for X-ray crystallographic analysis of CCGs. We could not prepare crystals of CCG-I suitable for X-ray crystallographic analysis because this compound formed fine powders under numerous recrystallization conditions.
  • 66
    • 0000646010 scopus 로고
    • A short hydrogen bond between near identical carboxyl group in the α modification of L-glutamic acid
    • - (Tor 1 = -173.0°, Tor 2 = -73.1°), respectively, (a) Lehmann, M. S.; Nunes, A. C. A short hydrogen bond between near identical carboxyl group in the α modification of L-glutamic acid. Acta Crystallogr. 1980, B36, 1621-1625. (b) Lehmann, M. S.; Koetzle, T. F.; Hamilton, W. C. Precision neutron diffraction structure determination of protein and nucleic acid components. VIII: the crystal and molecular structure of the β-form of the amino acid L-glutamic acid. J. Crystallogr. Mol. Struct. 1972, 2, 225-233.
    • (1980) Acta Crystallogr. , vol.B36 , pp. 1621-1625
    • Lehmann, M.S.1    Nunes, A.C.2
  • 67
    • 0001694117 scopus 로고
    • Precision neutron diffraction structure determination of protein and nucleic acid components. VIII: The crystal and molecular structure of the β-form of the amino acid L-glutamic acid
    • - (Tor 1 = -173.0°, Tor 2 = -73.1°), respectively, (a) Lehmann, M. S.; Nunes, A. C. A short hydrogen bond between near identical carboxyl group in the α modification of L-glutamic acid. Acta Crystallogr. 1980, B36, 1621-1625. (b) Lehmann, M. S.; Koetzle, T. F.; Hamilton, W. C. Precision neutron diffraction structure determination of protein and nucleic acid components. VIII: the crystal and molecular structure of the β-form of the amino acid L-glutamic acid. J. Crystallogr. Mol. Struct. 1972, 2, 225-233.
    • (1972) J. Crystallogr. Mol. Struct. , vol.2 , pp. 225-233
    • Lehmann, M.S.1    Koetzle, T.F.2    Hamilton, W.C.3
  • 68
    • 0002651548 scopus 로고
    • NMR studies of solution conformation of physiologically active amino-acids
    • Bergmann, E., Pullman, B., Eds.; D. Reidel Publishing: Dordrecht
    • For previous conformational studies of glutamate, see: Ham, N. S. NMR studies of solution conformation of physiologically active amino-acids. In Molecular and Quantum Pharmacology; Bergmann, E., Pullman, B., Eds.; D. Reidel Publishing: Dordrecht, 1974; pp 261-268.
    • (1974) Molecular and Quantum Pharmacology , pp. 261-268
    • Ham, N.S.1
  • 69
    • 0002837109 scopus 로고
    • Conformationally constrained acidic amino acids as probes of glutamate receptors and transporters
    • Kozikowski, A. P., Ed.; Raven Press; New York
    • For a review describing proposed conformational requirements of glutamate receptors based on the known glutamate agonists, see: Chamberlin, R.; Bridges, R. Conformationally constrained acidic amino acids as probes of glutamate receptors and transporters. In Drug Design for Neuroscience; Kozikowski, A. P., Ed.; Raven Press; New York, 1993; pp 231-259.
    • (1993) Drug Design for Neuroscience , pp. 231-259
    • Chamberlin, R.1    Bridges, R.2
  • 70
    • 85033837549 scopus 로고    scopus 로고
    • note
    • 2c,5b,10d,19 although at high concentrations this compound binds to NMDA receptors. We believe that the extended partial structure of DCG-IV also contributes to its potent activity to mGluRs.
  • 72
    • 85033862695 scopus 로고    scopus 로고
    • note
    • The rms value of E and CCG-I (antiperiplanar conformer) was 0.117 Å.
  • 73
    • 0028341707 scopus 로고
    • A conformationally constrained competitive inhibitor of the sodium-dependent glutamate transporter in forebrain synaptosomes: L-anti-endo-3,4-methanopyrrolidine dicarboxylate
    • CMP-II and -III have already been synthesized and characterized as L-syn-exo-MPDC and L-anti-endo-MPDC, respectively. Bridges, R. J.; Levering, F. E.; Koch, H.; Cotman, C. W.; Chamberlin, A. R. A conformationally constrained competitive inhibitor of the sodium-dependent glutamate transporter in forebrain synaptosomes: L-anti-endo-3,4-methanopyrrolidine dicarboxylate. Neuroscience Lett. 1994, 174, 193-197.
    • (1994) Neuroscience Lett. , vol.174 , pp. 193-197
    • Bridges, R.J.1    Levering, F.E.2    Koch, H.3    Cotman, C.W.4    Chamberlin, A.R.5
  • 74
    • 85033865271 scopus 로고    scopus 로고
    • note
    • 2O).
  • 75
    • 85033868469 scopus 로고    scopus 로고
    • note
    • Unpublished observations using electrophysiological method in the new born rat isolated spinal cord. There would be many reasons why CMPs are inactive to the receptors (e.g., steric hindrance, transport difficulties, and no flexibility to change its conformation). These factors could not be ruled out by the present studies.
  • 76
    • 5244321678 scopus 로고
    • NMDA receptors: Agonists and competitive antagonists
    • Sarel, S., Mechoulam, R., Agranat, I., Eds.; IUPAC/Blackwell Scientific Publications: New York
    • (a) Watkins, J. C. NMDA receptors: agonists and competitive antagonists. In Trends in Medicinal Chemistry, 90; Sarel, S., Mechoulam, R., Agranat, I., Eds.; IUPAC/Blackwell Scientific Publications: New York, 1992; pp 17-29.
    • (1992) Trends in Medicinal Chemistry, 90 , pp. 17-29
    • Watkins, J.C.1
  • 77
    • 0003131895 scopus 로고
    • Agonists and competitive antagonists: Structure-activity and molecular modelling studies
    • Watkins, J. C., Collingridge, G. L., Eds.; Oxford University Press: London
    • (b) Jane, D. E.; Olverman, H. J.; Watkins, J. C. Agonists and competitive antagonists: Structure-activity and molecular modelling studies. In The NMDA receptor, 2nd ed.; Watkins, J. C., Collingridge, G. L., Eds.; Oxford University Press: London, 1994; pp 31-104.
    • (1994) The NMDA Receptor, 2nd Ed. , pp. 31-104
    • Jane, D.E.1    Olverman, H.J.2    Watkins, J.C.3
  • 78
    • 0026774926 scopus 로고
    • Molecular modelling of N-methyl-L-aspartate receptor agonists
    • (a) O'Callaghan, D.; Wong, M. G.; Beart, P. M. Molecular modelling of N-methyl-L-aspartate receptor agonists. Mol. Neuropharmacol. 1992, 2, 89-92.
    • (1992) Mol. Neuropharmacol. , vol.2 , pp. 89-92
    • O'Callaghan, D.1    Wong, M.G.2    Beart, P.M.3
  • 80
    • 0026681096 scopus 로고
    • Generation of N-methyl-D-aspartate agonists and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists
    • Ortwine, D. F.; Malone, T. C.; Bigge, C. F.; Drummond, J. T.; Humblet, C.; Johnson, G.; Pinter, G. W. Generation of N-methyl-D-aspartate agonists and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists. J. Med. Chem. 1992, 35, 1345-1370.
    • (1992) J. Med. Chem. , vol.35 , pp. 1345-1370
    • Ortwine, D.F.1    Malone, T.C.2    Bigge, C.F.3    Drummond, J.T.4    Humblet, C.5    Johnson, G.6    Pinter, G.W.7
  • 82
    • 0025171558 scopus 로고
    • Synthesis and activity of a potent N-methyl-D-aspartic acid agonist, trans-1-aminocyclobutane-1,3-dicarboxylic acid, and related phosphonic and carboxylic acids
    • (b) Allan, R. D.; Hanrahan, J. R.; Hambley, T. W.; Johnston, G. A. R.; Mewett, K. N.; Mitrovic, A. D. Synthesis and activity of a potent N-methyl-D-aspartic acid agonist, trans-1-aminocyclobutane-1,3-dicarboxylic acid, and related phosphonic and carboxylic acids. J. Med. Chem. 1990, 33, 2905-2915.
    • (1990) J. Med. Chem. , vol.33 , pp. 2905-2915
    • Allan, R.D.1    Hanrahan, J.R.2    Hambley, T.W.3    Johnston, G.A.R.4    Mewett, K.N.5    Mitrovic, A.D.6
  • 83
    • 85033841560 scopus 로고    scopus 로고
    • note
    • The rms values of I and L with CCG-IV (antiperiplanar conformer) were 0.078 and 0.280 Å, respectively.
  • 84
    • 85033843708 scopus 로고    scopus 로고
    • note
    • 2O).
  • 86
    • 0011843373 scopus 로고
    • Synthesis and neuroexcitatory activity of new kainoids
    • Lubec, G., Rosenthal, G. A., Eds.; ESCOM: Leiden
    • (b) Hashimoto, K.; Shirahama, H. Synthesis and neuroexcitatory activity of new kainoids. In Amino acids: Chemistry, Biology and Medicine; Lubec, G., Rosenthal, G. A., Eds.; ESCOM: Leiden, 1990; pp 566-572.
    • (1990) Amino Acids: Chemistry, Biology and Medicine , pp. 566-572
    • Hashimoto, K.1    Shirahama, H.2
  • 87
    • 0025824599 scopus 로고
    • Novel kainate derivatives: Potent depolarizing actions on spinal motoneurones and dorsal root fibers in newborn rats
    • (c) Ishida, M.; Shinozaki, H. Novel kainate derivatives: potent depolarizing actions on spinal motoneurones and dorsal root fibers in newborn rats. Br. J. Pharmacol. 1991, 104, 873-878.
    • (1991) Br. J. Pharmacol. , vol.104 , pp. 873-878
    • Ishida, M.1    Shinozaki, H.2
  • 88
    • 0000196167 scopus 로고
    • Action of willardiin analogues on immature rat dosal root
    • (a) Blake, J. F.; Jane, D. E.; Watkins, J. C. Action of willardiin analogues on immature rat dosal root. Br. J. Pharmacol. 1991, 104, 334P. Wong, L. A.; Mayer, M. L.; Jane, D. E.; Watkins, J. C. Willardiines differentiate agonist binding site for kainate-versus AMPA-preferring glutamate receptors in DRG and hippocampal neurones. J. Neurosci. 1994, 14, 3881-3897.
    • (1991) Br. J. Pharmacol. , vol.104
    • Blake, J.F.1    Jane, D.E.2    Watkins, J.C.3
  • 89
    • 0028357664 scopus 로고
    • Willardiines differentiate agonist binding site for kainate-versus AMPA-preferring glutamate receptors in DRG and hippocampal neurones
    • (a) Blake, J. F.; Jane, D. E.; Watkins, J. C. Action of willardiin analogues on immature rat dosal root. Br. J. Pharmacol. 1991, 104, 334P. Wong, L. A.; Mayer, M. L.; Jane, D. E.; Watkins, J. C. Willardiines differentiate agonist binding site for kainate-versus AMPA-preferring glutamate receptors in DRG and hippocampal neurones. J. Neurosci. 1994, 14, 3881-3897.
    • (1994) J. Neurosci. , vol.14 , pp. 3881-3897
    • Wong, L.A.1    Mayer, M.L.2    Jane, D.E.3    Watkins, J.C.4
  • 90
    • 0022979956 scopus 로고
    • The primary afferent depolarizing action of kainate in the rat
    • (a) Agrawal, S. G.; Evans, R. H. The primary afferent depolarizing action of kainate in the rat. Br. J. Pharmacol. 1986, 87, 345-355.
    • (1986) Br. J. Pharmacol. , vol.87 , pp. 345-355
    • Agrawal, S.G.1    Evans, R.H.2
  • 91
    • 0023180475 scopus 로고
    • A comparison of excitatory amino acid antagonists acting at primary afferent C fibres and motoneurons of the isolated spinal cord of the rat
    • (b) Evans, R. H.; Evans, S. J.; Pook, P. C.; Sunter, D. C. A comparison of excitatory amino acid antagonists acting at primary afferent C fibres and motoneurons of the isolated spinal cord of the rat. Br. J. Pharmacol. 1987, 91, 531-537.
    • (1987) Br. J. Pharmacol. , vol.91 , pp. 531-537
    • Evans, R.H.1    Evans, S.J.2    Pook, P.C.3    Sunter, D.C.4
  • 92
    • 0027244355 scopus 로고
    • Synthesis of L-2-(2-carboxy-4-methylenecyclopentyl)glycines (CPGs). Novel conformationally restricted glutamate analogues
    • Raghavan, S.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synthesis of L-2-(2-carboxy-4-methylenecyclopentyl)glycines (CPGs). Novel conformationally restricted glutamate analogues. Tetrahedron Lett. 1993, 34, 5765-5768.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5765-5768
    • Raghavan, S.1    Ishida, M.2    Shinozaki, H.3    Nakanishi, K.4    Ohfune, Y.5
  • 93
    • 85033854027 scopus 로고    scopus 로고
    • note
    • 54b
  • 94
    • 0020584891 scopus 로고
    • 3H]kainic acid
    • 3H]kainic acid. Brain Res. 1983, 265, 169-172. (b) Conway, G. A.; Park, J. S.; Maggiora, L.; Mertes, M. P.; Gallon, N. Palladium(II) catalyzed olefin-coupling reactions of kainic acid: effects of substitution on the isopropenyl group on receptor binding. J. Med. Chem. 1984, 27, 52-56.
    • (1983) Brain Res. , vol.265 , pp. 169-172
    • Selvin, J.T.1    Collins, J.F.2    Coyle, J.T.3
  • 95
    • 0021364566 scopus 로고
    • Palladium(II) catalyzed olefin-coupling reactions of kainic acid: Effects of substitution on the isopropenyl group on receptor binding
    • 3H]kainic acid. Brain Res. 1983, 265, 169-172. (b) Conway, G. A.; Park, J. S.; Maggiora, L.; Mertes, M. P.; Gallon, N. Palladium(II) catalyzed olefin-coupling reactions of kainic acid: effects of substitution on the isopropenyl group on receptor binding. J. Med. Chem. 1984, 27, 52-56.
    • (1984) J. Med. Chem. , vol.27 , pp. 52-56
    • Conway, G.A.1    Park, J.S.2    Maggiora, L.3    Mertes, M.P.4    Gallon, N.5
  • 96
    • 85033868808 scopus 로고    scopus 로고
    • note
    • 57 In addition, the C3′R substituent of trans-MCG-IV is essential to activate kainate receptors where CCG-IV and cis-MCG-IV were inactive.
  • 97
    • 0026569392 scopus 로고
    • Heterocyclic excitatory amino acids. Synthesis and Biological activity of novel analogues of AMPA
    • (a) Madsen, U.; Wong, E. H. F. Heterocyclic excitatory amino acids. Synthesis and Biological activity of novel analogues of AMPA. J. Med. Chem. 1992, 107-111.
    • (1992) J. Med. Chem. , pp. 107-111
    • Madsen, U.1    Wong, E.H.F.2
  • 98
    • 37049082189 scopus 로고
    • Excitatory amino acids. Synthesis of (RS)-2-amino-3-(5-cyclopropyl-3-hydroxyisoxazol-4-yl)propionic acid, a new potent and specific AMPA receptor agonist
    • (b) Skjaerbaek, N.; Ebert, B.; Falch, E.; Brehm, L.; Krogsgaard-Larsen, P. Excitatory amino acids. Synthesis of (RS)-2-amino-3-(5-cyclopropyl-3-hydroxyisoxazol-4-yl)propionic acid, a new potent and specific AMPA receptor agonist. J. Chem. Soc., Perkin Trans I 1995, 221-225.
    • (1995) J. Chem. Soc., Perkin Trans I , pp. 221-225
    • Skjaerbaek, N.1    Ebert, B.2    Falch, E.3    Brehm, L.4    Krogsgaard-Larsen, P.5
  • 99
    • 0013128505 scopus 로고
    • Conformational and pharmacological characterization of 4-AHCP, a bicyclic homologue of the excitatory amino acid receptor agonist AMPA
    • (c) Lund, T. M.; Madsen, U.; Ebert, B.; Jorgensen, F. S.; Krogsgaard-Larsen, P. Conformational and pharmacological characterization of 4-AHCP, a bicyclic homologue of the excitatory amino acid receptor agonist AMPA. Med. Chem. Res. 1991, 1, 136-141.
    • (1991) Med. Chem. Res. , vol.1 , pp. 136-141
    • Lund, T.M.1    Madsen, U.2    Ebert, B.3    Jorgensen, F.S.4    Krogsgaard-Larsen, P.5
  • 100
    • 0025117827 scopus 로고
    • 2,3-Dihydroxy-6-nitro-7-sulfamoylbenzo(F)-quinoline: A neuroprotectant for cereberal ischemia
    • (a) Sheardown, M. J.; Nielsen, E. Ø.; Hansen, A. J.; Jacobsen, P.; Honoré, T. 2,3-Dihydroxy-6-nitro-7-sulfamoylbenzo(F)-quinoline: A neuroprotectant for cereberal ischemia. Science 1990, 247, 571-574.
    • (1990) Science , vol.247 , pp. 571-574
    • Sheardown, M.J.1    Nielsen, E.Ø.2    Hansen, A.J.3    Jacobsen, P.4    Honoré, T.5
  • 101
    • 0027529881 scopus 로고
    • A comparison of the actions of agonists and antagonists at non-NMDA receptors of C-fibers and motoneurones of the immature rat spinal cord in vivo
    • (b) Pook, P.; Brugger, F.; Hawkins, N. S.; Clark, K. C.; Watkins, J. C.; Evans, R. H. A comparison of the actions of agonists and antagonists at non-NMDA receptors of C-fibers and motoneurones of the immature rat spinal cord in vivo. Br. J. Phramacol. 1993, 108, 179-184.
    • (1993) Br. J. Phramacol. , vol.108 , pp. 179-184
    • Pook, P.1    Brugger, F.2    Hawkins, N.S.3    Clark, K.C.4    Watkins, J.C.5    Evans, R.H.6
  • 102
    • 84908806186 scopus 로고
    • Efficient synthesis of 4-methylene-L-glutamic acid and its analogues
    • Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Efficient synthesis of 4-methylene-L-glutamic acid and its analogues. Synlett 1993, 409-410.
    • (1993) Synlett , pp. 409-410
    • Ouerfelli, O.1    Ishida, M.2    Shinozaki, H.3    Nakanishi, K.4    Ohfune, Y.5
  • 103
    • 0027992583 scopus 로고
    • Phenylglycine derivatives as antagonists of metabotropic glutamate receptors
    • (a) Watkins, J. C.; Collingridge, G. C. Phenylglycine derivatives as antagonists of metabotropic glutamate receptors. Trends Pharmacol. Sci. 1994, 15, 333-342.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 333-342
    • Watkins, J.C.1    Collingridge, G.C.2
  • 104
    • 0028928489 scopus 로고
    • Metabotropic glutamate receptors: Novel targets for drug development
    • (b) Knöphel, T.; Kuhn, R.; Allgeier, H. Metabotropic glutamate receptors: Novel targets for drug development. J. Med. Chem. 1995, 38, 1417-1426.
    • (1995) J. Med. Chem. , vol.38 , pp. 1417-1426
    • Knöphel, T.1    Kuhn, R.2    Allgeier, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.