메뉴 건너뛰기




Volumn 39, Issue 24, 1996, Pages 4738-4743

Diastereoselective synthesis of all four isomers of 3-(4-chlorophenyl)glutamic acid: Identification of the isomers responsible for the potentiation of L-homocysteic acid-evoked depolarizations in neonatal rat motoneurons

Author keywords

[No Author keywords available]

Indexed keywords

2,4 PYRROLIDINEDICARBOXYLIC ACID; 3 (4 CHLOROPHENYL)GLUTAMIC ACID; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR AGONIST; GLUTAMATE RECEPTOR ANTAGONIST; HOMOCYSTEIC ACID; NEUROTRANSMITTER; UNCLASSIFIED DRUG;

EID: 0030478029     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960382c     Document Type: Article
Times cited : (10)

References (23)
  • 2
    • 0022534519 scopus 로고
    • In vitro release and electrophysiological effects in situ of homocysteic acid, an endogenous N-methyl-(D)-aspartic acid agonist in mammalian striatum
    • Do, K. Q.; Herrling, P. L.; Streit, P.; Turski, W. A.; Cuénod, M. In vitro release and electrophysiological effects in situ of homocysteic acid, an endogenous N-methyl-(D)-aspartic acid agonist in mammalian striatum. J. Neurosci. 1986, 6, 2226-2234.
    • (1986) J. Neurosci. , vol.6 , pp. 2226-2234
    • Do, K.Q.1    Herrling, P.L.2    Streit, P.3    Turski, W.A.4    Cuénod, M.5
  • 3
    • 0026032668 scopus 로고
    • The Influence of assay conditions on measurement of excitatory dibasic sulphinic and sulphonic alpha-amino acids in nervous tissue
    • Waller, S. J.; Kilpatrick, I. C.; Chan, M. W. J.; Evans, R. H. The Influence of assay conditions on measurement of excitatory dibasic sulphinic and sulphonic alpha-amino acids in nervous tissue. J. Neurosci. Methods 1991, 36, 167-176.
    • (1991) J. Neurosci. Methods , vol.36 , pp. 167-176
    • Waller, S.J.1    Kilpatrick, I.C.2    Chan, M.W.J.3    Evans, R.H.4
  • 6
    • 0022003354 scopus 로고
    • Selective potentiating effect of β-p-chlorophenylglutamate on responses induced by certain sulphur-containing excitatory amino acids and quisqualate
    • Davies, J.; Francis, A. A.; Oakes, D. J.; Sheardown, M. J.; Watkins, J. C. Selective potentiating effect of β-p-chlorophenylglutamate on responses induced by certain sulphur-containing excitatory amino acids and quisqualate. Neuropharmacology 1985, 24, 177-180.
    • (1985) Neuropharmacology , vol.24 , pp. 177-180
    • Davies, J.1    Francis, A.A.2    Oakes, D.J.3    Sheardown, M.J.4    Watkins, J.C.5
  • 7
    • 0023819535 scopus 로고
    • (±)-β-Para chlorophenylglutamate selectively enhances the depolarizing response to L-homocysteic acid in neocortical neurons of the rat: Evidence for a specific uptake system
    • Zeise, M. L.; Knöpfel, T.; Zieglgänsberger, W. (±)-β-Para chlorophenylglutamate selectively enhances the depolarizing response to L-homocysteic acid in neocortical neurons of the rat: evidence for a specific uptake system. Brain Res. 1988, 443, 373-376.
    • (1988) Brain Res. , vol.443 , pp. 373-376
    • Zeise, M.L.1    Knöpfel, T.2    Zieglgänsberger, W.3
  • 8
    • 0025891998 scopus 로고
    • L-Homocysteic acid mediates synaptic excitation at NMDA receptors in the hippocampus
    • Ito, S.; Provini, L.; Cherubini, E. L-Homocysteic acid mediates synaptic excitation at NMDA receptors in the hippocampus. Neurosci. Lett. 1991, 124, 157-161.
    • (1991) Neurosci. Lett. , vol.124 , pp. 157-161
    • Ito, S.1    Provini, L.2    Cherubini, E.3
  • 11
    • 0026597010 scopus 로고
    • Decreased glutamate transport by the brain and spinal cord in amyotrophic lateral sclerosis
    • Rothstein, J. D.; Martin, L. J.; Kuncl, R. W. Decreased glutamate transport by the brain and spinal cord in amyotrophic lateral sclerosis. N. Engl. J. Med. 1992, 326, 1464-1468.
    • (1992) N. Engl. J. Med. , vol.326 , pp. 1464-1468
    • Rothstein, J.D.1    Martin, L.J.2    Kuncl, R.W.3
  • 12
    • 0003416750 scopus 로고
    • Asymmetric derivitization of glycine
    • Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, U.K.
    • Williams, R. M. Asymmetric derivitization of glycine. In Synthesis of optically active α-amino acids, 1st ed.; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press: Oxford, U.K., 1989; pp 1-33.
    • (1989) Synthesis of Optically Active α-Amino Acids, 1st Ed. , pp. 1-33
    • Williams, R.M.1
  • 13
    • 0023626901 scopus 로고
    • Diastereoselective and enantioselective total synthesis of the hepatoprotective agent clausenamide
    • Hartwig, W.; Born, L. Diastereoselective and enantioselective total synthesis of the hepatoprotective agent clausenamide. J. Org. Chem. 1987, 52, 4352-4358.
    • (1987) J. Org. Chem. , vol.52 , pp. 4352-4358
    • Hartwig, W.1    Born, L.2
  • 14
    • 0022997891 scopus 로고
    • Asymmetric synthesis via heterocyclic intermediates; XXX. Asymmetric synthesis of glutamic acids and derivatives thereof by the bislactim-ether method. Michael-addition of methyl 2-alkenoates to the lithiated bislactim-ether of cyclo-(L-Val-Gly)
    • Schöllkopf, U.; Pettig, D.; Busse, U.; Egert, E.; Dyrbusch, M. Asymmetric synthesis via heterocyclic intermediates; XXX. Asymmetric synthesis of glutamic acids and derivatives thereof by the bislactim-ether method. Michael-addition of methyl 2-alkenoates to the lithiated bislactim-ether of cyclo-(L-Val-Gly). Synthesis 1986, 737-740.
    • (1986) Synthesis , pp. 737-740
    • Schöllkopf, U.1    Pettig, D.2    Busse, U.3    Egert, E.4    Dyrbusch, M.5
  • 15
    • 0025187613 scopus 로고
    • Direct resolution of some phenylglycines by liquid chromatography on a chiral crown ether phase
    • HPLC analysis was carried out using a Crownpak CR(+) column (150 x 4 mm, Daicel Chemical Industries Ltd., Tokyo, Japan) maintained at 3°C. The mobile phase was 1% perchloric acid run at 0.4 mL/min and the solutes were detected at 210 nm. The four isomers of chlorpheg (5-8) exhibited the following capacity factors: 39.9 (5), 44.4 (8), 53.4 (6), 74.7 (7). The separation factor (a) between the first and second eluted isomers (the critical pair separation) was 1.11 and the resolution factor was 1.25. Further details of the chromatographic behavior of these compounds will be published elsewhere. For details of the use of Crownpak columns, see: Udvarhelyi, P. M.; Watkins, J. C. Direct resolution of some phenylglycines by liquid chromatography on a chiral crown ether phase. Chirality 1990, 2, 200-204.
    • (1990) Chirality , vol.2 , pp. 200-204
    • Udvarhelyi, P.M.1    Watkins, J.C.2
  • 16
    • 0018270714 scopus 로고
    • 2+-like selective antagonism of excitatory amino acid-induced responses by α,ε-diaminopimelic acid, D-α-aminoadipate and HA-966 in isolated spinal cord of frog and immature rat
    • 2+-like selective antagonism of excitatory amino acid-induced responses by α,ε-diaminopimelic acid, D-α-aminoadipate and HA-966 in isolated spinal cord of frog and immature rat. Brain Res. 1978, 148, 536-542.
    • (1978) Brain Res. , vol.148 , pp. 536-542
    • Evans, R.H.1    Francis, A.A.2    Watkins, J.C.3
  • 17
    • 0026440686 scopus 로고
    • Neuronal and glial plasma membrane carrier-mediated uptake of L-homocysteate is not selectively blocked by β-p-chlorophenylglutamate
    • Griffiths, R.; Grieve, A.; Allan, S.; Olverman, H. J. Neuronal and glial plasma membrane carrier-mediated uptake of L-homocysteate is not selectively blocked by β-p-chlorophenylglutamate. Neurosci. Lett. 1992, 147, 175-178.
    • (1992) Neurosci. Lett. , vol.147 , pp. 175-178
    • Griffiths, R.1    Grieve, A.2    Allan, S.3    Olverman, H.J.4
  • 18
    • 0026080845 scopus 로고
    • Conformationally defined neurotransmitter analogues. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer
    • Bridges, R. J.; Stanley, M. S.; Anderson, M. W.; Cotman, C. W.; Chamberlin, A. R. Conformationally defined neurotransmitter analogues. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer. J. Med.Chem. 1991, 34, 717-725.
    • (1991) J. Med.Chem. , vol.34 , pp. 717-725
    • Bridges, R.J.1    Stanley, M.S.2    Anderson, M.W.3    Cotman, C.W.4    Chamberlin, A.R.5
  • 19
    • 0029620310 scopus 로고
    • Differential actions of 3-(4-chlorophenyl)glutamic acid stereoisomers and L-trans-pyrrolidine-2,4-dicarboxylic acid upon L-homocysteic acid- and L-glutamic acid-induced responses from rat spinal motoneurones
    • A fuller account of the pharmacological characterization of 5-8 has been published: Chalmers, D. J.; Jane, D. E.; Sunter, D. C.; Thompson, G. A.; Udvarhelyi, P. M.; Kilpatrick, I. C.; Watkins, J. C. Differential actions of 3-(4-chlorophenyl)glutamic acid stereoisomers and L-trans-pyrrolidine-2,4-dicarboxylic acid upon L-homocysteic acid- and L-glutamic acid-induced responses from rat spinal motoneurones. Neuropharmacology 1995, 34, 1589-1595.
    • (1995) Neuropharmacology , vol.34 , pp. 1589-1595
    • Chalmers, D.J.1    Jane, D.E.2    Sunter, D.C.3    Thompson, G.A.4    Udvarhelyi, P.M.5    Kilpatrick, I.C.6    Watkins, J.C.7
  • 20
    • 5544268071 scopus 로고
    • Phenylpropiolic acid
    • Wiley: New York
    • Abbot, T. W. Phenylpropiolic acid. Organic Synthesis; Wiley: New York, 1943; Vol. II, pp 515-517.
    • (1943) Organic Synthesis , vol.2 , pp. 515-517
    • Abbot, T.W.1
  • 21
    • 0011859055 scopus 로고
    • Rates of hydrolysis of cis- and trans-3- and 4-substituted ethyl cinnamates
    • Bloomfield, J. J.; Fuchs, R. Rates of hydrolysis of cis- and trans-3- and 4-substituted ethyl cinnamates. J. Org. Chem. 1961, 26, 2991-2993.
    • (1961) J. Org. Chem. , vol.26 , pp. 2991-2993
    • Bloomfield, J.J.1    Fuchs, R.2
  • 22
    • 84985516415 scopus 로고
    • Enantioselective synthesis of (R)-amino acids using L-valine as chiral agent
    • Schöllkopf, U.; Groth, U.; Deng, C. Enantioselective synthesis of (R)-amino acids using L-valine as chiral agent. Angew. Chem., Int. Ed. Engl. 1981, 20, 798-799.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 798-799
    • Schöllkopf, U.1    Groth, U.2    Deng, C.3
  • 23
    • 0020062045 scopus 로고
    • The effects of a series of ω-phosphonic α-carboxylic acids on electrically evoked and excitant amino acid-induced responses in isolated spinal cord preparations
    • Evans, R. H.; Francis, A. A.; Jones, A. W.; Smith, D. A. S.; Watkins, J. C. The effects of a series of ω-phosphonic α-carboxylic acids on electrically evoked and excitant amino acid-induced responses in isolated spinal cord preparations. Br. J. Pharmacol. 1982, 75, 65-75.
    • (1982) Br. J. Pharmacol. , vol.75 , pp. 65-75
    • Evans, R.H.1    Francis, A.A.2    Jones, A.W.3    Smith, D.A.S.4    Watkins, J.C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.