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Volumn 43, Issue 4, 2000, Pages 706-720

A new class of conformationally rigid analogues of 4-amino-5- halopentanoic acids, potent inactivators of γ-aminobutyric acid aminotransferase

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 2 BROMO 4 FLUOROCYCLOPENTANE 1 CARBOXYLIC ACID; 3 AMINO 2,4 DIBROMOCYCLOPENTANE 1 CARBOXYLIC ACID; 3 AMINO 4 BROMO 2 FLUOROCYCLOPENTANE 1 CARBOXYLIC ACID; 3 AMINO 4 BROMOCYCLOPENTANE 1 CARBOXYLIC ACID; 3 AMINO 4 FLUOROCYCLOPENTANE 1 CARBOXYLIC ACID; 3ALPHA AMINO 2BETA BROMO 4BETA HYDROXYCYCLOPENTANE 1ALPHA CARBOXYLIC ACID; 3ALPHA AMINO 2BETA BROMOCYCLOPENTANE 1ALPHA CARBOXYLIC ACID; 3ALPHA AMINO 4BETA BROMO 2BETA HYDROXYCYCLOPENTANE 1ALPHA CARBOXYLIC ACID; 3BETA AMINO 4,4 DIFLUOROCYCLOPENTANE 1BETA CARBOXYLIC ACID; 4 AMINO 5 FLUOROVALERIC ACID; 4 AMINOBUTYRATE AMINOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE; VIGABATRIN;

EID: 0034001395     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9904755     Document Type: Article
Times cited : (120)

References (35)
  • 1
    • 0011921009 scopus 로고
    • The γ-aminobutyric acid-α-ketoglutaric acid transaminase of bee brain
    • Baxter, C. F.; Roberts, E. J. The γ-Aminobutyric Acid-α-ketoglutaric acid Transaminase of Bee Brain. J. Biol. Chem. 1958, 233, 1135-1139.
    • (1958) J. Biol. Chem. , vol.233 , pp. 1135-1139
    • Baxter, C.F.1    Roberts, E.J.2
  • 2
    • 0017714634 scopus 로고
    • Effect of ethanolamine-O-sulphate on regional GABA metabolism in the mouse brain
    • (a) Leach, M, J.; Walker, J. M. G. Effect of Ethanolamine-O-sulphate on Regional GABA Metabolism in the Mouse Brain. Biochem. Pharmacol. 1977, 26, 1569-1572.
    • (1977) Biochem. Pharmacol. , vol.26 , pp. 1569-1572
    • Leach, M.J.1    Walker, J.M.G.2
  • 3
    • 0019974023 scopus 로고
    • The effects of sodium valproate on γ-aminobutyrate metabolism and behaviour in naive and ethanolamine-O-sulphate pretreated rats and mice
    • (b) Phillips, N. I.; Fowler, L. J. The Effects of Sodium Valproate on γ-Aminobutyrate Metabolism and Behaviour in Naive and Ethanolamine-O-sulphate Pretreated Rats and Mice. Biochem. Pharmacol. 1982, 31, 2257-2261.
    • (1982) Biochem. Pharmacol. , vol.31 , pp. 2257-2261
    • Phillips, N.I.1    Fowler, L.J.2
  • 4
    • 0024459858 scopus 로고
    • GABA in epilepsy: The pharmacological basis
    • Gale, K. GABA in Epilepsy: the Pharmacological Basis. Epilepsia 1989, 30 (Suppl 3), S1-S11.
    • (1989) Epilepsia , vol.30 , Issue.3 SUPPL.
    • Gale, K.1
  • 5
    • 0032765110 scopus 로고    scopus 로고
    • The irreversible gamma-aminobutyric acid (GABA) transaminase inhibitor gamma-vinyl-GABA blocks cocaine self-administration in rats
    • Kushner, S. A.; Dewey, S. L.; Kornetsky, C. The Irreversible gamma-Aminobutyric Acid (GABA) Transaminase Inhibitor gamma-Vinyl-GABA Blocks Cocaine Self-Administration in Rats. J. Pharmacol. Exp. Ther. 1999, 290, 797-802.
    • (1999) J. Pharmacol. Exp. Ther. , vol.290 , pp. 797-802
    • Kushner, S.A.1    Dewey, S.L.2    Kornetsky, C.3
  • 6
    • 0024447161 scopus 로고
    • Design of potential anticolvulsant agents: Mechanistic classification of GABA aminotransferase inactivators
    • Nanavati, S. M.; Silverman, R. B. Design of Potential Anticolvulsant Agents: Mechanistic Classification of GABA Aminotransferase Inactivators. J. Med. Chem. 1989, 32, 2413-2421.
    • (1989) J. Med. Chem. , vol.32 , pp. 2413-2421
    • Nanavati, S.M.1    Silverman, R.B.2
  • 7
    • 0018413924 scopus 로고
    • Affinity labeling of alanine aminotransferase by 3-chloro-L-alanine
    • Morino, Y.; Kojima, H.; Tanase, S. Affinity Labeling of Alanine Aminotransferase by 3-Chloro-L-alanine, J. Biol. Chem. 1979, 254, 279-285.
    • (1979) J. Biol. Chem. , vol.254 , pp. 279-285
    • Morino, Y.1    Kojima, H.2    Tanase, S.3
  • 8
    • 0017854719 scopus 로고
    • Suicide substrates for the alanine racemase of Escherichia Coli B
    • Wang, E.; Walsh, C. Suicide Substrates for the Alanine Racemase of Escherichia Coli B. Biochemistry 1978, 17, 1313-1321.
    • (1978) Biochemistry , vol.17 , pp. 1313-1321
    • Wang, E.1    Walsh, C.2
  • 9
    • 0015967027 scopus 로고
    • Affinity labeling of the active center of L-aspartate-β-decarboxylase with β-chloro-L-alanine
    • Relyea, N. M.; Tate, S. S.; Meister, A. Affinity Labeling of the Active Center of L-Aspartate-β-decarboxylase with β-chloro-L-alanine. J. Biol. Chem. 1974, 249, 1519-1524.
    • (1974) J. Biol. Chem. , vol.249 , pp. 1519-1524
    • Relyea, N.M.1    Tate, S.S.2    Meister, A.3
  • 10
    • 0018889370 scopus 로고
    • Synthesis of (S)-5-substituted 4-aminopentanoic acids: A new class of γ-aminobutyric acid transaminase inactivators
    • (a) Silverman, R. B.; Levy, M. A. Synthesis of (S)-5-Substituted 4-Aminopentanoic Acids: A New Class of γ-Aminobutyric Acid Transaminase Inactivators. J. Org. Chem. 1980, 45, 815-818.
    • (1980) J. Org. Chem. , vol.45 , pp. 815-818
    • Silverman, R.B.1    Levy, M.A.2
  • 11
    • 0019326956 scopus 로고
    • Irreversible inactivation of pig brain γ-aminobutyric acid-α-ketoglutarate transaminase by 4-amino-5-halopentanoic acids
    • (b) Silverman, R. B.; Levy, M. A. Irreversible Inactivation of Pig Brain γ-Aminobutyric Acid-α-ketoglutarate Transaminase by 4-Amino-5-halopentanoic Acids. Biochem. Biophys. Res. Commun. 1980, 95, 250-255.
    • (1980) Biochem. Biophys. Res. Commun. , vol.95 , pp. 250-255
    • Silverman, R.B.1    Levy, M.A.2
  • 12
    • 0019871861 scopus 로고
    • Mechanism of inactivation of γ-aminobutyric acid-α-ketoglutaric acid aminotransferase by 4-amino-5-halopentanoic acids
    • Silverman, R. B.; Levy, M. A. Mechanism of Inactivation of γ-Aminobutyric Acid-α-Ketoglutaric Acid Aminotransferase by 4-Amino-5-halopentanoic Acids. Biochemistry 1981, 20, 1197-1203.
    • (1981) Biochemistry , vol.20 , pp. 1197-1203
    • Silverman, R.B.1    Levy, M.A.2
  • 13
    • 0022972790 scopus 로고
    • Mechanism of inactivation of γ-aminobutyrate aminotransferase by 4-amino-5-fluoropentanoic acid. First example of an enamine mechanism for γ-amino acid with a partition ratio of 0
    • Silverman, R. B.; Invergo, B. J. Mechanism of Inactivation of γ-Aminobutyrate Aminotransferase by 4-Amino-5-fluoropentanoic Acid. First Example of an Enamine Mechanism for γ-Amino Acid with a Partition Ratio of 0. Biochemistry 1986, 25, 6817-6820.
    • (1986) Biochemistry , vol.25 , pp. 6817-6820
    • Silverman, R.B.1    Invergo, B.J.2
  • 14
    • 0026347939 scopus 로고
    • Mechanisms of inactivation of γ-aminobutyric acid aminotransferase by the antiepilepsy drug γ-vinyl GABA (vigabatrin)
    • Nanavati, S. M.; Silverman, R. B. Mechanisms of Inactivation of γ-Aminobutyric Acid Aminotransferase by the Antiepilepsy Drug γ-Vinyl GABA (Vigabatrin). J. Am. Chem. Soc. 1991,113, 9341-9349.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9341-9349
    • Nanavati, S.M.1    Silverman, R.B.2
  • 15
    • 0033523938 scopus 로고    scopus 로고
    • Inhibition and substrate activity of conformationally-rigid vigabatrin analogues with γ-aminobutyric acid aminotransferase
    • Qiu, J.; Pingsterhaus, J.; Silverman, R. B. Inhibition and Substrate Activity of Conformationally-Rigid Vigabatrin Analogues with γ-Aminobutyric Acid Aminotransferase J. Med. Chem. 1999, 42, 4725-4728.
    • (1999) J. Med. Chem. , vol.42 , pp. 4725-4728
    • Qiu, J.1    Pingsterhaus, J.2    Silverman, R.B.3
  • 17
    • 37049077169 scopus 로고
    • Rearrangement of 2-azabicyclo[2.2.1]hept-5-en-3-ones: Synthesis of cis3-aminocyclopentane carboxylic acid derivatives
    • Palmer, C. F.; Parry, K, P.; Roberts, S. M.; Sik, V. Rearrangement of 2-Azabicyclo[2.2.1]hept-5-en-3-ones: Synthesis of cis3-Aminocyclopentane Carboxylic Acid Derivatives. J. Chem. Soc., Perkin Trans. 1 1992, 1021-1028.
    • (1992) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1021-1028
    • Palmer, C.F.1    Parry, K.P.2    Roberts, S.M.3    Sik, V.4
  • 18
    • 33847800447 scopus 로고
    • New fluorinating reagents. Dialkylaminosulfur fluorides
    • Middleton, W. New Fluorinating Reagents. Dialkylaminosulfur Fluorides. J. Org. Chem. 1975, 40, 574-578.
    • (1975) J. Org. Chem. , vol.40 , pp. 574-578
    • Middleton, W.1
  • 20
    • 0021154272 scopus 로고
    • Stereospecfic synthesis of chiral precursor of thienamycin from L-threonine
    • Shiozaki, M.; Ishida, N.; Hiraoka, T.; Marayuma, H. Stereospecfic Synthesis of Chiral Precursor of Thienamycin from L-Threonine Tetrahedron 1984, 40, 1795-1802.
    • (1984) Tetrahedron , vol.40 , pp. 1795-1802
    • Shiozaki, M.1    Ishida, N.2    Hiraoka, T.3    Marayuma, H.4
  • 22
    • 0002169605 scopus 로고    scopus 로고
    • A new approach to the synthesis of aristolactams. Total synthesis of cepharanone A and B
    • Couture, A.; Deniau, E.; Grandclaudon, P.; Lebrun, S. A New Approach to the Synthesis of Aristolactams. Total Synthesis of Cepharanone A and B. Synlett 1997, 1475-1477.
    • (1997) Synlett , pp. 1475-1477
    • Couture, A.1    Deniau, E.2    Grandclaudon, P.3    Lebrun, S.4
  • 23
    • 0031575786 scopus 로고    scopus 로고
    • A highly efficient synthesis of the antiviral agent (+)-cycloaradine involving the regioselective cleavage of epoxide by neighboring participation
    • Katagiri, N.; Matsuhashi, Y.; Kokufuda, H.; Takebayashi, M.; Kaneko, C. A Highly Efficient Synthesis of the Antiviral Agent (+)-Cycloaradine Involving the Regioselective Cleavage of Epoxide by Neighboring Participation. Tetrahedron Lett. 1997, 38, 1961-1964.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1961-1964
    • Katagiri, N.1    Matsuhashi, Y.2    Kokufuda, H.3    Takebayashi, M.4    Kaneko, C.5
  • 25
    • 85022673348 scopus 로고
    • Syn-7-norbornenyl toluene-sulfonate
    • (a) Winstein, S.; Stafford, J. Syn-7-Norbornenyl Toluene-sulfonate. J. Am. Chem. Soc. 1957, 79, 505-507.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 505-507
    • Winstein, S.1    Stafford, J.2
  • 26
    • 0009083897 scopus 로고
    • Reaction of exo-norbornylene oxide with hydrogen bromide
    • (b) Walborsky, H. M.; Loncrini, D. F. Reaction of Exo-norbornylene Oxide with Hydrogen Bromide. J. Org. Chem. 1957, 22, 1117-1119.
    • (1957) J. Org. Chem. , vol.22 , pp. 1117-1119
    • Walborsky, H.M.1    Loncrini, D.F.2
  • 27
    • 0019799682 scopus 로고
    • ω-fluoromethyl analogues of ω-amino acids as irreversible inhibitors of 4-aminobutyrate: 2-oxoglutarate aminotransferase
    • Bey, P.; Jung, M. J.; Gerhart, F.; Schirlin, D.; Van Dorsselaer, V.; Casara, P. ω-Fluoromethyl Analogues of ω-Amino Acids as Irreversible Inhibitors of 4-Aminobutyrate: 2-Oxoglutarate Aminotransferase. J. Neurochem. 1981, 37, 1341-1344.
    • (1981) J. Neurochem. , vol.37 , pp. 1341-1344
    • Bey, P.1    Jung, M.J.2    Gerhart, F.3    Schirlin, D.4    Van Dorsselaer, V.5    Casara, P.6
  • 28
    • 0019888652 scopus 로고
    • Substituted 4-aminobutanoic acids: Substrates for γ-aminobutyric acid α-ketoglutaric acid aminotransferase
    • Silverman, R. B.; Levy, M. A. Substituted 4-Aminobutanoic Acids: Substrates for γ-Aminobutyric Acid α-Ketoglutaric Acid Aminotransferase J. Biol. Chem. 1981, 256, 11565-11568.
    • (1981) J. Biol. Chem. , vol.256 , pp. 11565-11568
    • Silverman, R.B.1    Levy, M.A.2
  • 29
    • 0343986481 scopus 로고    scopus 로고
    • Multiple active enzyme species of γ-aminobutyric acid aminotransferase are not isozymes
    • submitted
    • Koo, Y. K.; Nandi, D.; Silverman, R. B. Multiple Active Enzyme Species of γ-Aminobutyric Acid Aminotransferase are not Isozymes. Arch. Biochem. Biophys., submitted.
    • Arch. Biochem. Biophys.
    • Koo, Y.K.1    Nandi, D.2    Silverman, R.B.3
  • 31
    • 84965093141 scopus 로고
    • Soluble γ-aminobutyric-glutamic transaminase from Pseudomonas Fluorescens W. B
    • Scott, E. M.; Jakoby, W. B. Soluble γ-Aminobutyric-Glutamic Transaminase from Pseudomonas Fluorescens W. B. J. Biol. Chem. 1959, 234, 932-936.
    • (1959) J. Biol. Chem. , vol.234 , pp. 932-936
    • Scott, E.M.1    Jakoby, W.B.2
  • 34
    • 0003518480 scopus 로고
    • John Wiley & Sons: New York;
    • Segal, I. H. Enzyme Kinetics; John Wiley & Sons: New York; 1975; p 106.
    • (1975) Enzyme Kinetics , pp. 106
    • Segal, I.H.1
  • 35
    • 0017368370 scopus 로고
    • i by beef heart mitochondrial adenosine triphosphatase
    • i by Beef Heart Mitochondrial Adenosine Triphosphatase. J. Biol. Chem. 1977, 252, 2891-2899.
    • (1977) J. Biol. Chem. , vol.252 , pp. 2891-2899
    • Penefsky, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.