메뉴 건너뛰기




Volumn 48, Issue 8, 2005, Pages 3026-3035

Novel cyclopropyl β-amino acid analogues of pregabalin and gabapentin that target the α2-δ protein

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOMETHYLSPIRO[2.5]OCTANE 1 CARBOXYLIC ACID; ALPHA2 DELTA PROTEIN; AMPHOLYTE; BETA AMINO ACID; CYCLOPROPYL AMINO ACID; CYCLOPROPYL BETA AMINO ACID DERIVATIVE; ESTER; GABAPENTIN; KETONE; LEUCINE; NEUTRAL AMINO ACID; NITROALKANE; PREGABALIN; PROTEIN; UNCLASSIFIED DRUG; VOLTAGE GATED CALCIUM CHANNEL;

EID: 20944435741     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0491086     Document Type: Article
Times cited : (43)

References (33)
  • 3
    • 0035144675 scopus 로고    scopus 로고
    • Pregabalin may represent a novel class of anxiolytic agents with a broad spectrum of activity
    • Field, M. J.; Oles, R. J.; Singh, L. Pregabalin may represent a novel class of anxiolytic agents with a broad spectrum of activity. Br. J. Pharmacol. 2001, 132, 1-4.
    • (2001) Br. J. Pharmacol. , vol.132 , pp. 1-4
    • Field, M.J.1    Oles, R.J.2    Singh, L.3
  • 4
    • 0029975930 scopus 로고    scopus 로고
    • The novel anticonvulsant drug, gabapentin (Neurontin), binds to the α2δ subunit of a calcium channel
    • Gee, N. S.; Brown, J. P.; Dissanayake, V. U. K.; Offord, J.; Thurlow, R.; Woodruff, G. N. The novel anticonvulsant drug, gabapentin (Neurontin), binds to the α2δ subunit of a calcium channel. J. Biol. Chem. 1998, 271 (10), 5768.
    • (1998) J. Biol. Chem. , vol.271 , Issue.10 , pp. 5768
    • Gee, N.S.1    Brown, J.P.2    Dissanayake, V.U.K.3    Offord, J.4    Thurlow, R.5    Woodruff, G.N.6
  • 6
    • 0033965974 scopus 로고    scopus 로고
    • +-evoked glutamate release from rat neocortical and hippocampal slices by gabapentin
    • +-evoked glutamate release from rat neocortical and hippocampal slices by gabapentin. Neurosci. Lett. 2000, 280 (2), 107.
    • (2000) Neurosci. Lett. , vol.280 , Issue.2 , pp. 107
    • Dooley, D.J.1    Mieske, C.A.2    Borosky, S.A.3
  • 7
    • 0033696481 scopus 로고    scopus 로고
    • 3H]norepinephrine release from rat neocortical slices by gabapentin and pregabalin
    • 3H]norepinephrine release from rat neocortical slices by gabapentin and pregabalin. J. Pharmacol. Exp. Ther. 2000, 295 (3), 1086.
    • (2000) J. Pharmacol. Exp. Ther. , vol.295 , Issue.3 , pp. 1086
    • Dooley, D.J.1    Donovan, C.M.2    Pugsley, T.A.3
  • 8
    • 0034972502 scopus 로고    scopus 로고
    • 3H]glutamate from rat caudal trigeminal nucleus slices
    • 3H]glutamate from rat caudal trigeminal nucleus slices. Pain 2001, 93 (2), 191.
    • (2001) Pain , vol.93 , Issue.2 , pp. 191
    • Maneuf, Y.P.1    Hughes, J.2    McKnight, A.T.3
  • 9
    • 12944281498 scopus 로고    scopus 로고
    • A study comparing the actions of gabapentin and pregabalin on the electrophysiological properties of cultured DRG neurones from neonatal rats
    • McClelland, D.; Evans, R. M.; Barkworth, L.; Martin, D. J.; Scott, R. H. A study comparing the actions of gabapentin and pregabalin on the electrophysiological properties of cultured DRG neurones from neonatal rats. BMC Pharmacology 2004, 4 (14).
    • (2004) BMC Pharmacology , vol.4 , Issue.14
    • McClelland, D.1    Evans, R.M.2    Barkworth, L.3    Martin, D.J.4    Scott, R.H.5
  • 11
    • 0033018825 scopus 로고    scopus 로고
    • 3-Substituted GABA analogues with central nervous system activity: A review
    • Bryans, J. S.; Wustrow, D. J. 3-Substituted GABA analogues with central nervous system activity: a review. Med. Res. Rev. 1999, 19 (2), 149.
    • (1999) Med. Res. Rev. , vol.19 , Issue.2 , pp. 149
    • Bryans, J.S.1    Wustrow, D.J.2
  • 17
    • 0348241858 scopus 로고
    • A tandem Michael reaction-cycloalkylation utilizing 2-nitropropane: A facile route to the acid component of insecticidal pyrethroids
    • Babler, J. H.; Spina, K. P. A tandem Michael reaction-cycloalkylation utilizing 2-nitropropane: A facile route to the acid component of insecticidal pyrethroids. Tetrahedron Lett. 1985, 26, 1923.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1923
    • Babler, J.H.1    Spina, K.P.2
  • 18
    • 0038221292 scopus 로고
    • Nitro compounds as nucleophilic alkylidene transfer reagents
    • Ono, N.; Tetsuya, Y.; Isami, H.; Kamimura, A.; Kaji, A. Nitro compounds as nucleophilic alkylidene transfer reagents. J. Org. Chem. 1985, 50 (15), 2806. The methyl ester of compound 5 is disclosed in this paper.
    • (1985) J. Org. Chem. , vol.50 , Issue.15 , pp. 2806
    • Ono, N.1    Tetsuya, Y.2    Isami, H.3    Kamimura, A.4    Kaji, A.5
  • 19
    • 85083233215 scopus 로고
    • Cyclopropanation of electrophilic alkenes with nitroalkanes in the presence of alumina-supported potassium fluoride
    • Mélot, J.-M.; Texier-Boullet, F.; Foucaud, A. Cyclopropanation of electrophilic alkenes with nitroalkanes in the presence of alumina-supported potassium fluoride. Synthesis 1987, 364.
    • (1987) Synthesis , pp. 364
    • Mélot, J.-M.1    Texier-Boullet, F.2    Foucaud, A.3
  • 20
    • 0033575678 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of conformationally restricted gabapentin analogues
    • references therein. See also ref 20
    • For other reports describing constrained gabapentin and pregabalin analogues, see: Receveur, J.-M.; Bryans, J. S.; Field, M. J.; Singh, L.; Horwell, D. C. Synthesis and biological evaluation of conformationally restricted gabapentin analogues. Bioorg. Med. Chem. Lett. 1999, 9, 2329, and references therein. See also ref 20.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2329
    • Receveur, J.-M.1    Bryans, J.S.2    Field, M.J.3    Singh, L.4    Horwell, D.C.5
  • 21
    • 0035939112 scopus 로고    scopus 로고
    • Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers
    • Ling, R.; Ekhato, I. V.; Rubin, J. R.; Wustrow, D. J. Synthesis of 4-alkyl-pyrrolidine-3-carboxylic acid stereoisomers. Tetrahedron 2001, 57 (30), 6579.
    • (2001) Tetrahedron , vol.57 , Issue.30 , pp. 6579
    • Ling, R.1    Ekhato, I.V.2    Rubin, J.R.3    Wustrow, D.J.4
  • 22
    • 0000271946 scopus 로고
    • Reduction of organic compounds with sodium borohydride-transition metal salt systems (1). Reduction of organic nitrile, nitro, and amide compounds to primary amines
    • Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Reduction of organic compounds with sodium borohydride-transition metal salt systems (1). Reduction of organic nitrile, nitro, and amide compounds to primary amines. Tetrahedron Lett. 1969, (52), 4555.
    • (1969) Tetrahedron Lett. , Issue.52 , pp. 4555
    • Satoh, T.1    Suzuki, S.2    Suzuki, Y.3    Miyaji, Y.4    Imai, Z.5
  • 23
    • 0002624346 scopus 로고    scopus 로고
    • Cyclopropyl building blocks for organic synthesis, 49. Convenient preparation of α-amino acids with bicyclopropylidene and other methylenecyclopropane moieties
    • and references therein
    • For the preparation of related cyclopropyl amino acids see: Brandl, M.; Kozhushkov, S. I.; Yufit, D. S.; Howard, J. A. K.; de Meijere, A. Cyclopropyl building blocks for organic synthesis, 49. convenient preparation of α-amino acids with bicyclopropylidene and other methylenecyclopropane moieties. Eur. J. Org. Chem. 1998, (12), 2785, and references therein.
    • (1998) Eur. J. Org. Chem. , Issue.12 , pp. 2785
    • Brandl, M.1    Kozhushkov, S.I.2    Yufit, D.S.3    Howard, J.A.K.4    De Meijere, A.5
  • 24
    • 17444399551 scopus 로고    scopus 로고
    • note
    • Attempts to fashion the tris-cyclopropyl amino acid failed at the Knoevenagel condensation stage with the sterically encumbered dicyclopropyl ketone. (diagram presented)
  • 25
    • 0042699922 scopus 로고    scopus 로고
    • Efficient enantioconvergent synthesis of (S)-α-benzyl-α- methyl-β-alanine from (-R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid
    • Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A.; Gil, A. Efficient enantioconvergent synthesis of (S)-α-benzyl-α- methyl-β-alanine from (-R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid. Tetrahedron: Asymmetry 2003, 14, 2209-2214.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2209-2214
    • Badorrey, R.1    Cativiela, C.2    Diaz-De-Villegas, M.D.3    Gálvez, J.A.4    Gil, A.5
  • 26
    • 0034723238 scopus 로고    scopus 로고
    • Practical asymmetric synthesis of (S)-MA20565, a wide-spectrum agricultural fungicide
    • The direct chlorination of α-methylbenzyl alcohols with methanesulfonyl chloride/pyridine was found to found to proceed in a solvent-dependent fashion: Tanaka, K.; Katsurada, M.; Ohno, F.; Shiga, Y.; Oda, M.; Miyagi, M.; Takehara, J.; Okano, K. Practical Asymmetric Synthesis of (S)-MA20565, a Wide-Spectrum Agricultural Fungicide. J. Org. Chem. 2000, 65, 432.
    • (2000) J. Org. Chem. , vol.65 , pp. 432
    • Tanaka, K.1    Katsurada, M.2    Ohno, F.3    Shiga, Y.4    Oda, M.5    Miyagi, M.6    Takehara, J.7    Okano, K.8
  • 27
    • 85064263262 scopus 로고
    • Novel synthesis of 1-cyanocyclopropane-1-carboxylic acid and its application to the synthesis of amino acids containing cyclopropane rings
    • Ohno, M.; Tanaka, H.; Komatsu, M.; Ohshiro, Y. Novel synthesis of 1-cyanocyclopropane-1-carboxylic acid and its application to the synthesis of amino acids containing cyclopropane rings. Synlett 1991, 919.
    • (1991) Synlett , pp. 919
    • Ohno, M.1    Tanaka, H.2    Komatsu, M.3    Ohshiro, Y.4
  • 28
    • 0028986069 scopus 로고
    • Transport of gabapentin, a γ-amino acid drug, by system L α-amino acid transporters: A comparative study in astrocytes, synaptosomes, and CHO cells
    • Su, T.-Z.; Lunney, E.; Campbell, G.; Oxender, D. Transport of gabapentin, a γ-amino acid drug, by system L α-amino acid transporters: a comparative study in astrocytes, synaptosomes, and CHO cells. J. Neurochemistry 1995, 64, 2125-2131.
    • (1995) J. Neurochemistry , vol.64 , pp. 2125-2131
    • Su, T.-Z.1    Lunney, E.2    Campbell, G.3    Oxender, D.4
  • 29
    • 0348131419 scopus 로고
    • The genetics and biochemistry of audiogenic seizures
    • G., Theissen, D. D., Eds. Appleton-Century-Crofts, New York
    • Schlesinger, K.; Greik, B. J. The genetics and biochemistry of audiogenic seizures in: Contributions to Behavior-Genetic Analysis: The Mouse as a Prototype Lindzey, G., Theissen, D. D., Eds. Appleton-Century-Crofts, New York 1970, 219-257; Seyford, T. N. Audiogenic Seizures in Mice. Fed. Proc. 1979, 38, 2399.
    • (1970) Contributions to Behavior-Genetic Analysis: The Mouse as a Prototype Lindzey , pp. 219-257
    • Schlesinger, K.1    Greik, B.J.2
  • 30
    • 0018696499 scopus 로고
    • Audiogenic seizures in mice
    • Schlesinger, K.; Greik, B. J. The genetics and biochemistry of audiogenic seizures in: Contributions to Behavior-Genetic Analysis: The Mouse as a Prototype Lindzey, G., Theissen, D. D., Eds. Appleton-Century-Crofts, New York 1970, 219-257; Seyford, T. N. Audiogenic Seizures in Mice. Fed. Proc. 1979, 38, 2399.
    • (1979) Fed. Proc. , vol.38 , pp. 2399
    • Seyford, T.N.1
  • 31
    • 0036064894 scopus 로고    scopus 로고
    • Synthesis of substituted cyclopropylphosphonates by Michael induced ring closure (MIRC) reactions
    • Stevens, C. V.; Van Heecke, G.; Barbero, C.; Patora, K.; De Kimpe, N.; Verhe, R. Synthesis of substituted cyclopropylphosphonates by Michael induced ring closure (MIRC) reactions. Synlett. 2002, (7), 1089.
    • (2002) Synlett. , Issue.7 , pp. 1089
    • Stevens, C.V.1    Van Heecke, G.2    Barbero, C.3    Patora, K.4    De Kimpe, N.5    Verhe, R.6
  • 33
    • 0019796746 scopus 로고
    • Neutral amino acid transport systems in Chinese hamster ovary cells
    • Shotwell, M. A.; Jayme, D. W.; Elberg, M. S.; Oxender, D. L. Neutral amino acid transport systems in Chinese hamster ovary cells. J. Biol. Chem. 1981, 256 (11), 5422-7.
    • (1981) J. Biol. Chem. , vol.256 , Issue.11 , pp. 5422-5427
    • Shotwell, M.A.1    Jayme, D.W.2    Elberg, M.S.3    Oxender, D.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.