메뉴 건너뛰기




Volumn 36, Issue 12, 1993, Pages 1716-1725

The Synthesis of Novel GABA Uptake Inhibitors. 1. Elucidation of the Structure-Activity Studies Leading to the Choice of (R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic Acid (Tiagabine) as an Anticonvulsant Drug Candidate

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; GUVACINE DERIVATIVE; NIPECOTIC ACID DERIVATIVE; NNC 050328; TIAGABINE; UNCLASSIFIED DRUG;

EID: 0027241691     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00064a005     Document Type: Article
Times cited : (158)

References (69)
  • 1
    • 0022484695 scopus 로고
    • GABAergic Neurotransmission. An Overview
    • Racagni, G., Donoso, A., Eds.; Raven Press: New York
    • De Robertis, E. GABAergic Neurotransmission. An Overview. In GABA and Endocrine Function; Racagni, G., Donoso, A., Eds.; Raven Press: New York, 1987; pp 1–12.
    • (1987) GABA and Endocrine Function , pp. 1-12
    • De Robertis, E.1
  • 2
    • 0042920557 scopus 로고
    • GABAergic Neurons
    • Gottlieb, D. I. GABAergic Neurons. Sci. Am. 1988, 38–45.
    • (1988) Sci. Am. , pp. 38-45
    • Gottlieb, D.I.1
  • 3
    • 0001541773 scopus 로고
    • Biochemistry, Anatomy, and Pharmacology of GABA Neurons
    • Melzer, H. Y., Ed.; Raven Press: New York
    • Fonnum, F. Biochemistry, Anatomy, and Pharmacology of GABA Neurons. In Psychopharmacology: The Third Generation of Progress; Melzer, H. Y., Ed.; Raven Press: New York, 1987; pp 173–182.
    • (1987) Psychopharmacology: The Third Generation of Progress , pp. 173-182
    • Fonnum, F.1
  • 4
    • 0016590785 scopus 로고
    • Epilepsy and Gamma-aminobutyric Acid Mediated Inhibition
    • Meldrum, B. S. Epilepsy and Gamma-aminobutyric Acid Mediated Inhibition. Int. Rev. Neurobiol. 1975, 17, 1–36.
    • (1975) Int. Rev. Neurobiol. , vol.17 , pp. 1-36
    • Meldrum, B.S.1
  • 5
    • 0000662666 scopus 로고
    • GABAmimetics in Animal Models of Seizure States
    • (L.E.R.S. Monograph Series Vol. 3); Bartholom, G., Bossi, L., Lloyd, K. G., Morselli, P. L., Eds.; Raven Press: New York
    • Löscher, W. GABAmimetics in Animal Models of Seizure States. In Epilepsy and GABA Receptor Agonists Basic and Therapeutic Research (L.E.R.S. Monograph Series Vol. 3); Bartholom, G., Bossi, L., Lloyd, K. G., Morselli, P. L., Eds.; Raven Press: New York, 1985; pp 109–119.
    • (1985) Epilepsy and GABA Receptor Agonists Basic and Therapeutic Research , pp. 109-119
    • Löscher, W.1
  • 6
    • 0025653110 scopus 로고
    • Mechanism Based Approaches to Anticonvulsant Therapies: Modulation of Inhibitory and Excitatory Transmission
    • Wiley-Liss Inc.: New York
    • Meldrum, B. Mechanism Based Approaches to Anticonvulsant Therapies: Modulation of Inhibitory and Excitatory Transmission. In Current and Future Trends in Anticonvulsant, Anxiety, and Stroke Therapy; Wiley-Liss Inc.: New York, 1990; pp 31–43.
    • (1990) Current and Future Trends in Anticonvulsant, Anxiety, and Stroke Therapy , pp. 31-43
    • Meldrum, B.1
  • 7
    • 0012051256 scopus 로고
    • GABAergic Transmission in the Mammalian Central Nervous System
    • Krogsgaard-Larsen, P., Scheel-Krüger, J., Kofoed, H., Eds.; Munksgaard: Copenhagen
    • Curtis, D. R. GABAergic Transmission in the Mammalian Central Nervous System. In GABA-Neurotransmitters: Pharmacochemical Biochemical and Pharmacological Aspects; Krogsgaard-Larsen, P., Scheel-Krüger, J., Kofoed, H., Eds.; Munksgaard: Copenhagen, 1978; pp 17–27.
    • (1978) GABA-Neurotransmitters: Pharmacochemical Biochemical and Pharmacological Aspects , pp. 17-27
    • Curtis, D.R.1
  • 8
    • 0019454782 scopus 로고
    • GABA Receptor Pharmacology. Functional Considerations
    • Enna, S. J. GABA Receptor Pharmacology. Functional Considerations. Biochem. Pharmacol. 1981, 30, 907–913.
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 907-913
    • Enna, S.J.1
  • 9
    • 0019839152 scopus 로고
    • γ-Aminobutyric Acid Agonists, Antagonists, and Uptake Inhibitors. Design and Therapeutic Aspects
    • Krogsgaard-Larsen, P. γ-Aminobutyric Acid Agonists, Antagonists, and Uptake Inhibitors. Design and Therapeutic Aspects. J. Med. Chem. 1981, 24, 1377–1383.
    • (1981) J. Med. Chem. , vol.24 , pp. 1377-1383
    • Krogsgaard-Larsen, P.1
  • 10
    • 0001457952 scopus 로고
    • Recent Advances in GABA Agonists, Antagonists and Uptake Inhibitors: Structure-Activity Relationships and Therapeutic Potential
    • Krogsgaard-Larsen, P.; Hjeds, H.; Falch, E.; Joergensen, F. S.; Nielsen, L. Recent Advances in GABA Agonists, Antagonists and Uptake Inhibitors: Structure-Activity Relationships and Therapeutic Potential Adv. Drug. Res. 1988, 17, 381–456.
    • (1988) Adv. Drug. Res. , vol.17 , pp. 381-456
    • Krogsgaard-Larsen, P.1    Hjeds, H.2    Falch, E.3    Joergensen, F.S.4    Nielsen, L.5
  • 11
    • 0001480163 scopus 로고
    • Vigabatrin
    • Meldrum, B. S., Porter, R. J., Eds.; John Libby: London
    • Schechter, P. J. Vigabatrin. In New Anticonvulsant Drugs; Meldrum, B. S., Porter, R. J., Eds.; John Libby: London, 1986; pp 265–275.
    • (1986) New Anticonvulsant Drugs , pp. 265-275
    • Schechter, P.J.1
  • 14
    • 0023848467 scopus 로고
    • GABA Synaptic Mechanisms: Stereochemical and Conformational Requirements
    • Krogsgaard-Larsen, P. GABA Synaptic Mechanisms: Stereochemical and Conformational Requirements. Med. Res. Rev. 1988, 8, 27–56.
    • (1988) Med. Res. Rev. , vol.8 , pp. 27-56
    • Krogsgaard-Larsen, P.1
  • 15
    • 0020521271 scopus 로고
    • Effects of THIP on Chronic Anxiety
    • Hoehn-Saric, R. Effects of THIP on Chronic Anxiety. Psychopharmacology 1983, 80, 338–341.
    • (1983) Psychopharmacology , vol.80 , pp. 338-341
    • Hoehn-Saric, R.1
  • 16
    • 0021336316 scopus 로고
    • Novel Inhibitors of γ-Aminobutyric Acid (GABA) Uptake: Anticonvulsant Actions in Rats and Mice
    • Yunger, L. M.; Fowler, P. J.; Zarevics, P.; Setler, P. E. Novel Inhibitors of γ-Aminobutyric Acid (GABA) Uptake: Anticonvulsant Actions in Rats and Mice. J. Pharm. Exp. Ther. 1984, 228, 109–115.
    • (1984) J. Pharm. Exp. Ther. , vol.228 , pp. 109-115
    • Yunger, L.M.1    Fowler, P.J.2    Zarevics, P.3    Setler, P.E.4
  • 17
    • 0021998836 scopus 로고
    • Anticonvulsant Action in the Epileptic Gerbil of Novel Inhibitors of GABA Uptake
    • Löscher, W. Anticonvulsant Action in the Epileptic Gerbil of Novel Inhibitors of GABA Uptake. Eur. J. Pharmacol. 1985, 110, 103–108.
    • (1985) Eur. J. Pharmacol. , vol.110 , pp. 103-108
    • Löscher, W.1
  • 18
    • 0022263023 scopus 로고
    • Comparison of the Anticonvulsant Effects of Two Novel GABA Uptake Inhibitors and Diazepam in Amygdaloid Kindled Rats
    • Schwark, W. S.; Löscher, W. Comparison of the Anticonvulsant Effects of Two Novel GABA Uptake Inhibitors and Diazepam in Amygdaloid Kindled Rats. Naunyn-Schmiedeberg's Arch. Pharmacol. 1985, 329, 367–371.
    • (1985) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.329 , pp. 367-371
    • Schwark, W.S.1    Löscher, W.2
  • 19
    • 0023713608 scopus 로고
    • Anticonvulsant Effects of Localized Chronic Infusions of GABA in Cortical and Reticular Structures of Baboons
    • Silva-Barrat, C.; Brailowsky, S.; Riche, D.; Menini, C. Anticonvulsant Effects of Localized Chronic Infusions of GABA in Cortical and Reticular Structures of Baboons. Exp. Neurol. 1988, 101, 418–427.
    • (1988) Exp. Neurol. , vol.101 , pp. 418-427
    • Silva-Barrat, C.1    Brailowsky, S.2    Riche, D.3    Menini, C.4
  • 20
    • 0002998479 scopus 로고
    • GABA Uptake Inhibitors as Experimental Tools and Potential Drugs in Epilepsy Research
    • Morselli, P., Lloyd, K. G., Löscher, W., Meldrum, B. S., Reynolds, E. H., Eds.; Raven Press: New York
    • Krogsgaard-Larsen, P.; Labouta, I. M.; Meldrum, B.; Croucher, M.; Schousboe, A. GABA Uptake Inhibitors as Experimental Tools and Potential Drugs in Epilepsy Research. In Neurotransmitters, Seizures and Epilepsy; Morselli, P., Lloyd, K. G., Löscher, W., Meldrum, B. S., Reynolds, E. H., Eds.; Raven Press: New York, 1981; pp 23–25.
    • (1981) Neurotransmitters, Seizures and Epilepsy , pp. 23-25
    • Krogsgaard-Larsen, P.1    Labouta, I.M.2    Meldrum, B.3    Croucher, M.4    Schousboe, A.5
  • 21
    • 0025122262 scopus 로고
    • GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry, and Enantioselectivity of (R)-(−)-and (S)-(+)-Homo-β-proline
    • Nielsen, L.; Brehm, L.; Krogsgaard-Larsen, P. GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry, and Enantioselectivity of (R)-(−)-and (S)-(+)-Homo-β-proline. J. Med. Chem. 1990, 33, 71–77.
    • (1990) J. Med. Chem. , vol.33 , pp. 71-77
    • Nielsen, L.1    Brehm, L.2    Krogsgaard-Larsen, P.3
  • 23
    • 0003010982 scopus 로고
    • Blood-Brain Barrier: Techniques for the Intracerebral Administration of Drugs
    • Iversen, L. L., Iversen, S. D., Snyder, S. H., Eds.; Plenum Press: New York
    • Myers, R. D. Blood-Brain Barrier: Techniques for the Intracerebral Administration of Drugs. In Handbook of Pharmacology, Vol. II; Iversen, L. L., Iversen, S. D., Snyder, S. H., Eds.; Plenum Press: New York, 1975; pp 1–28.
    • (1975) Handbook of Pharmacology , vol.2 , pp. 1-28
    • Myers, R.D.1
  • 24
    • 0020314516 scopus 로고
    • Problems of Delivery of Drugs to the Brain
    • Bodor, N.; Brewster, M. E. Problems of Delivery of Drugs to the Brain. Pharmacol. Ther. 1983, 19, 337–386.
    • (1983) Pharmacol. Ther. , vol.19 , pp. 337-386
    • Bodor, N.1    Brewster, M.E.2
  • 25
    • 0018386217 scopus 로고
    • Influence of Inhibitors of High Affinity GABA Uptake on Seizure Thresholds in Mice
    • Frey, H.-H.; Popp, C.; Löscher, W. Influence of Inhibitors of High Affinity GABA Uptake on Seizure Thresholds in Mice. Neuropharmacology 1979, 18, 581–590.
    • (1979) Neuropharmacology , vol.18 , pp. 581-590
    • Frey, H.-H.1    Popp, C.2    Löscher, W.3
  • 26
    • 0023920282 scopus 로고
    • A Comparison of Prodrug Esters of Nipecotic Acid
    • Hinko, C. N.; Crider, A. M.; Wood, J. D. A Comparison of Prodrug Esters of Nipecotic Acid. Neuropharmacology 1988, 27, 475–483.
    • (1988) Neuropharmacology , vol.27 , pp. 475-483
    • Hinko, C.N.1    Crider, A.M.2    Wood, J.D.3
  • 28
    • 0023897574 scopus 로고
    • Which Animal Models Should Be Used in the Search for New Antiepileptic Drugs? A Proposal Based on Experimental and Clinical Considerations
    • Löscher, W.; Schmidt, D. Which Animal Models Should Be Used in the Search for New Antiepileptic Drugs? A Proposal Based on Experimental and Clinical Considerations. Epilepsy Res. 1988, 2, 145–181.
    • (1988) Epilepsy Res. , vol.2 , pp. 145-181
    • Löscher, W.1    Schmidt, D.2
  • 29
    • 0023177523 scopus 로고
    • Prophylaxis of Amygdala-Kindling Induced Epileptogenesis: Comparison of a GABA Uptake Inhibitor and Diazepam
    • Schwark, W.; Haluska, M. Prophylaxis of Amygdala-Kindling Induced Epileptogenesis: Comparison of a GABA Uptake Inhibitor and Diazepam. Epilepsy Res. 1987, 1, 63–69.
    • (1987) Epilepsy Res. , vol.1 , pp. 63-69
    • Schwark, W.1    Haluska, M.2
  • 30
    • 0026012420 scopus 로고
    • GABA Uptake Inhibitors: Construction of a General Pharmacophore Model and Successful Prediction of a New Representative
    • N'Goka, V.; Schlewer, G.; Linget, J.-M.; Chambon, J.-P.; Wermuth, C.-G. GABA Uptake Inhibitors: Construction of a General Pharmacophore Model and Successful Prediction of a New Representative. J. Med. Chem. 1991, 34, 2547–2557.
    • (1991) J. Med. Chem. , vol.34 , pp. 2547-2557
    • N'Goka, V.1    Schlewer, G.2    Linget, J.-M.3    Chambon, J.-P.4    Wermuth, C.-G.5
  • 33
    • 0025662980 scopus 로고
    • Pharmacology of CI-966: A Potent GABA Uptake Inhibitor, In Vitro and in Experimental Animals
    • Taylor, C. P.; Vartanian, M. G.; Schwarz, R. D.; Rock, D. M.; Callahan, M. J.; Davis, M. D. Pharmacology of CI-966: A Potent GABA Uptake Inhibitor, In Vitro and in Experimental Animals. Drug Dev. Res. 1990, 21, 195–215.
    • (1990) Drug Dev. Res. , vol.21 , pp. 195-215
    • Taylor, C.P.1    Vartanian, M.G.2    Schwarz, R.D.3    Rock, D.M.4    Callahan, M.J.5    Davis, M.D.6
  • 34
    • 0025607760 scopus 로고
    • GABA Receptors and GABAergic Synapses as Targets for Drug Development
    • Taylor, C. P. GABA Receptors and GABAergic Synapses as Targets for Drug Development. Drug Dev. Res. 1990, 21, 151–160.
    • (1990) Drug Dev. Res. , vol.21 , pp. 151-160
    • Taylor, C.P.1
  • 38
    • 0025060943 scopus 로고
    • The Effect of Two Lipophilic γ-Aminobutyric Acid Uptake Blockers in CA1 of the Rat Hippocampal Slice
    • Rekling, J. C.; Jahnsen, H.; Mosfeldt Laursen, A. The Effect of Two Lipophilic γ-Aminobutyric Acid Uptake Blockers in CA1 of the Rat Hippocampal Slice. Br. J. Pharmacol. 1990, 99, 103–106.
    • (1990) Br. J. Pharmacol. , vol.99 , pp. 103-106
    • Rekling, J.C.1    Jahnsen, H.2    Mosfeldt Laursen, A.3
  • 39
    • 0005221237 scopus 로고
    • Anticonvulsant Tolerance and Recovery During Repeated Administration of the GABA Uptake Inhibitor NO-328
    • (Proc. Suppl. April), Abstract 131P
    • Picardo, A.; Gent, P.; Feely, M. Anticonvulsant Tolerance and Recovery During Repeated Administration of the GABA Uptake Inhibitor NO-328. Br. J. Pharmacol. 1990, 99 (Proc. Suppl. April), Abstract 131P.
    • (1990) Br. J. Pharmacol. , vol.99
    • Picardo, A.1    Gent, P.2    Feely, M.3
  • 40
    • 0344889831 scopus 로고
    • Analgesic Effect of the GABA Uptake Inhibitor NO-328 (N-[4,4-Di(3-methyl-2-thienyl)but-3-en-1-yl)nipecotic Acid. 19th Annual Meeting of the Society for Neuroscience, Phoenix, AZ, U.S.A., October 29–November 3, 1989
    • Sheardown, M. J.; Weis, J. U.; Knutsen, L. J. S.; Swedberg, M. D. B.; Suzdak, P. D. Analgesic Effect of the GABA Uptake Inhibitor NO-328 (N-[4,4-Di(3-methyl-2-thienyl)but-3-en-1-yl)nipecotic Acid. 19th Annual Meeting of the Society for Neuroscience, Phoenix, AZ, U.S.A., October 29–November 3, 1989. Soc. Neurosci. Abstr. 1989, 15, 602.
    • (1989) Soc. Neurosci. Abstr. , vol.15 , pp. 602
    • Sheardown, M.J.1    Weis, J.U.2    Knutsen, L.J.S.3    Swedberg, M.D.B.4    Suzdak, P.D.5
  • 41
    • 25044457361 scopus 로고
    • Anxiolytic effect of NO-328, a GABA Uptake Inhibitor
    • Nielsen, E. B. Anxiolytic effect of NO-328, a GABA Uptake Inhibitor. Psychopharmacology 1988, V96, N1, S42.
    • (1988) Psychopharmacology , vol.V96
    • Nielsen, E.B.1
  • 42
    • 0025295574 scopus 로고
    • Tolerance to the Cognitive Impairing Effects but not to the Anticonvulsant Effects of NO-328, a Selective GABA Uptake Inhibitor
    • Judge, M. E.; Swedberg, M. D. B.; Suzdak, P. D. Tolerance to the Cognitive Impairing Effects but not to the Anticonvulsant Effects of NO-328, a Selective GABA Uptake Inhibitor. Eur. J. Pharmacol. 1990, 183, 467.
    • (1990) Eur. J. Pharmacol. , vol.183 , pp. 467
    • Judge, M.E.1    Swedberg, M.D.B.2    Suzdak, P.D.3
  • 43
    • 0001814745 scopus 로고
    • Tiagabine Safety and Tolerance During 2-weeks Multiple Dosing to Healthy Volunteers
    • Mengel, H. B.; Pierce, M. W.; Mant, T.; Christensen, M. S.; Gustafson, L. Tiagabine Safety and Tolerance During 2-weeks Multiple Dosing to Healthy Volunteers. Epilepsia 1991, 32 (suppl. 1), 1991.
    • (1991) Epilepsia , vol.32 , pp. 1991
    • Mengel, H.B.1    Pierce, M.W.2    Mant, T.3    Christensen, M.S.4    Gustafson, L.5
  • 45
    • 84982382328 scopus 로고
    • Synthetic Oxytocics. I. 3-(Piperidyl-(N)-Methyl)indoles and Related Compounds
    • Akkerman, A. M.; De Jongh, D. K.; Veldstra, H. Synthetic Oxytocics. I. 3-(Piperidyl-(N)-Methyl)indoles and Related Compounds. Recl. Trav. Chim. Pays-Bos 1951, 70, 899–916.
    • (1951) Recl. Trav. Chim. Pays-Bos , vol.70 , pp. 899-916
    • Akkerman, A.M.1    De Jongh, D.K.2    Veldstra, H.3
  • 46
    • 0000892545 scopus 로고
    • Absolute Configuration and Optical Purity of 3-Substituted Piperidines
    • Bettoni, G.; Duranti, E.; Tortorella, V. Absolute Configuration and Optical Purity of 3-Substituted Piperidines. Gazz. Chim. Ital. 1972, 102, 189–195.
    • (1972) Gazz. Chim. Ital. , vol.102 , pp. 189-195
    • Bettoni, G.1    Duranti, E.2    Tortorella, V.3
  • 47
    • 0002666942 scopus 로고
    • Terpenes and Related Compounds From Methyl Cyclopropyl Ketone
    • Julia, M.; Julia, S.; Giegan, R. Terpenes and Related Compounds From Methyl Cyclopropyl Ketone. Bull. Soc. Chim. Fr. 1960, 1072–1079.
    • (1960) Bull. Soc. Chim. Fr. , pp. 1072-1079
    • Julia, M.1    Julia, S.2    Giegan, R.3
  • 48
    • 0001420064 scopus 로고
    • The Reaction of Trimethylchlorosilane with Alpha-cyclopropanoic Alcohols in the Presence or in the Absence of Lithium Halogenides
    • Balme, G.; Foumet, G.; Gore, J. The Reaction of Trimethylchlorosilane with Alpha-cyclopropanoic Alcohols in the Presence or in the Absence of Lithium Halogenides. Tetrahedron Lett. 1986, 27, 1907–1908.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1907-1908
    • Balme, G.1    Foumet, G.2    Gore, J.3
  • 49
    • 33947314974 scopus 로고
    • Acid-Catalyzed Brominations, Deuterations, Rearrangements, and De-brominations of Thiophenes under Mild Conditions
    • Kellogg, R. M.; Schaap, A. P.; Harper, E. T.; Wynberg, H. Acid-Catalyzed Brominations, Deuterations, Rearrangements, and De-brominations of Thiophenes under Mild Conditions. J. Org. Chem. 1968, 33, 2902–2909.
    • (1968) J. Org. Chem. , vol.33 , pp. 2902-2909
    • Kellogg, R.M.1    Schaap, A.P.2    Harper, E.T.3    Wynberg, H.4
  • 50
    • 33947298672 scopus 로고
    • The Reformatsky Reaction with Halolactones. I. Reaction with Nonsteroid Carbonyl Compounds
    • Torabi, H.; Evans, R. L.; Stavely, H. E. The Reformatsky Reaction with Halolactones. I. Reaction with Nonsteroid Carbonyl Compounds. J. Org. Chem. 1969, 34, 3792–3796.
    • (1969) J. Org. Chem. , vol.34 , pp. 3792-3796
    • Torabi, H.1    Evans, R.L.2    Stavely, H.E.3
  • 51
    • 84980117543 scopus 로고
    • Grignard Reactions with Haloalkylamines. III. Formation of Oxolanes by a New Ring Closure Reaction of 3-Dimethylaminopropylcarbinol
    • Marxer, A. Grignard Reactions with Haloalkylamines. III. Formation of Oxolanes by a New Ring Closure Reaction of 3-Dimethylaminopropylcarbinol. Helv. Chim. Acta 1969, 52, 262–270.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 262-270
    • Marxer, A.1
  • 52
    • 0016234869 scopus 로고
    • A Structural Modification Study of the Antimalarial 2-(p-Chlorophenyl)-2-(4-piperidinyl)tetrahydrofuran
    • McCaustland, D. J.; Chien, P.-L.; Burton, W. H.; Cheng, C. C. A Structural Modification Study of the Antimalarial 2-(p-Chlorophenyl)-2-(4-piperidinyl)tetrahydrofuran. J. Med. Chem. 1974, 17, 993–1000.
    • (1974) J. Med. Chem. , vol.17 , pp. 993-1000
    • McCaustland, D.J.1    Chien, P.-L.2    Burton, W.H.3    Cheng, C.C.4
  • 53
    • 0000813042 scopus 로고
    • Carbonylation of Aryllithium Agents in the Presence of Alkyl Halides: One-Pot Synthesis of Diarylalkylcarbinols and Derivatives
    • Nudelman, N. S.; Vitale, A. A. Carbonylation of Aryllithium Agents in the Presence of Alkyl Halides: One-Pot Synthesis of Diarylalkylcarbinols and Derivatives. J. Org. Chem. 1981, 46, 4625–4626.
    • (1981) J. Org. Chem. , vol.46 , pp. 4625-4626
    • Nudelman, N.S.1    Vitale, A.A.2
  • 56
    • 0003661053 scopus 로고
    • Preparation of Unsaturated Heterocyclic Compounds, II. Synthesis of Guvacine
    • Morlacchi, F.; Cardellini, M.; Liberatore, F. Preparation of Unsaturated Heterocyclic Compounds, II. Synthesis of Guvacine. Ann. Chim. 1967, 57, 1456–1461.
    • (1967) Ann. Chim. , vol.57 , pp. 1456-1461
    • Morlacchi, F.1    Cardellini, M.2    Liberatore, F.3
  • 57
    • 85022903472 scopus 로고    scopus 로고
    • Personal communication
    • Guddal, E. Personal communication.
    • Guddal, E.1
  • 58
    • 0025883092 scopus 로고
    • GABA Uptake Inhibitors. Syntheses and Structure-activity Studies on GABA Analogues Containing Diarybutenyl and Diarylmethoxy-alkyl N-substituents
    • Falch, E.; Krogsgaard-Larsen, P. GABA Uptake Inhibitors. Syntheses and Structure-activity Studies on GABA Analogues Containing Diarybutenyl and Diarylmethoxy-alkyl N-substituents. Eur. J. Med. Chem. 1991, 26, 69–78.
    • (1991) Eur. J. Med. Chem. , vol.26 , pp. 69-78
    • Falch, E.1    Krogsgaard-Larsen, P.2
  • 59
    • 0006989345 scopus 로고
    • Benzhydryl β-Chloroethyl Ether
    • Wiley: New York, Collect
    • Sugasawa, S.; Fujiwara, K. Benzhydryl β-Chloroethyl Ether. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 72.
    • (1963) Organic Syntheses , vol.4 , pp. 72
    • Sugasawa, S.1    Fujiwara, K.2
  • 62
    • 0017874744 scopus 로고
    • 3H]-GABA into Rat Brain Synaptosomes
    • 3H]-GABA into Rat Brain Synaptosomes. Acta Pharmacol. Toxicol. 1978, 42, 73–76.
    • (1978) Acta Pharmacol. Toxicol. , vol.42 , pp. 73-76
    • Fjalland, B.1
  • 63
    • 0025072222 scopus 로고
    • Cloning of the Human Brain GABA Transporter
    • Nelson, H.; Mandiyan, S.; Nelson, N. Cloning of the Human Brain GABA Transporter. FEBS Lett. 1990, 269, 181–184.
    • (1990) FEBS Lett. , vol.269 , pp. 181-184
    • Nelson, H.1    Mandiyan, S.2    Nelson, N.3
  • 65
    • 0025015348 scopus 로고
    • GABA Transporter Protein Cloned from Rat Brain
    • Bowery, N. G. GABA Transporter Protein Cloned from Rat Brain. Trends Pharmacol. Sci. 1990, 11, 435–437.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 435-437
    • Bowery, N.G.1
  • 66
    • 0025010033 scopus 로고
    • A GABA Transporter cDNA has been Cloned
    • Kuhar, M. A GABA Transporter cDNA has been Cloned. Trends Neurosci. 1990, 13, 473–474.
    • (1990) Trends Neurosci. , vol.13 , pp. 473-474
    • Kuhar, M.1
  • 67
    • 0023546523 scopus 로고
    • Hydrophobicity and Central Nervous System Agents: On the Principle of Minimal Hydrophobicity in Drug Design
    • Hansch, C.; Björkroth, J. P.; Leo, A. Hydrophobicity and Central Nervous System Agents: On the Principle of Minimal Hydrophobicity in Drug Design. J. Pharm. Sci. 1987, 76, 663–687.
    • (1987) J. Pharm. Sci. , vol.76 , pp. 663-687
    • Hansch, C.1    Björkroth, J.P.2    Leo, A.3
  • 68
    • 0002714675 scopus 로고
    • Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. J. Org. Chem. 1978, 43, 2923–2925.
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 69
    • 0002253332 scopus 로고
    • Extension of the Modified Stobbe Condensation. Acid-Catalyzed Decomposition of the Products and a Lacto-enoic Tautomerism
    • Johnson, W. S.; Petersen, J. W.; Schneider, W. P. Extension of the Modified Stobbe Condensation. Acid-Catalyzed Decomposition of the Products and a Lacto-enoic Tautomerism. J. Am. Chem. Soc. 1947, 69, 74–79.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 74-79
    • Johnson, W.S.1    Petersen, J.W.2    Schneider, W.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.