Facile synthesis of (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine, an isotype-selective agonist of metabotropic glutamate receptors

被引:29
|
作者
Ma, DW
Ma, ZC
机构
[1] Stt. Key Lab. Bio-Organ. Nat. P., Shanghai Inst. of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Lu
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(97)10037-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(2S,1'S,2'S)-2-(Carboxycyclopropyl)glycine (L-CCG-I) was synthesized in 12 steps and 14% overall yield by using Sharpless's asymmetric dihydroxylation reaction and stereochemically controlled cyclopropanation as key steps. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:7599 / 7602
页数:4
相关论文
共 50 条
  • [1] (2S,3S,4S)ALPHA-(CARBOXYCYCLOPROPYL)GLYCINE IS A NOVEL AGONIST OF METABOTROPIC GLUTAMATE RECEPTORS
    NAKAGAWA, Y
    SAITOH, K
    ISHIHARA, T
    ISHIDA, M
    SHINOZAKI, H
    EUROPEAN JOURNAL OF PHARMACOLOGY, 1990, 184 (01) : 205 - 206
  • [2] Depression of EPSCs of rat spinal motoneurones in vitro by the metabotropic glutamate receptor agonist (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine (LCCG-I)
    Gao, CQ
    Tse, HW
    Evans, RH
    Headley, PM
    Jane, DE
    JOURNAL OF PHYSIOLOGY-LONDON, 1996, 493P : P51 - P52
  • [3] (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a potent and selective antagonist of type 2 metabotropic glutamate receptors
    Thomsen, C
    Bruno, V
    Nicoletti, F
    Marinozzi, M
    Pellicciari, R
    MOLECULAR PHARMACOLOGY, 1996, 50 (01) : 6 - 9
  • [4] An efficient and stereoselective synthesis of (2S,1′S,2′S)-2-(carboxycyclopropyl) glycine (LCCG-I):: conformationally constrained L-glutamate analogues
    Pajouhesh, H
    Chen, J
    Pajouhesh, SH
    TETRAHEDRON-ASYMMETRY, 2000, 11 (22) : 4537 - 4541
  • [5] Isolation of pure (2S,1′S,2′S)-2-(2′-carboxycyclopropyl)glycine from Blighia sapida (Akee)
    Natalini, B
    Capodiferro, V
    De Luca, C
    Espinal, R
    JOURNAL OF CHROMATOGRAPHY A, 2000, 873 (02) : 283 - 286
  • [6] (2S,1′S,2′S,3′R)-2-(2′-carboxy-3′-methylcyclopropyl) glycine is a potent and selective metabotropic group 2 receptor agonist with anxiolytic properties
    Collado, I
    Pedregal, C
    Mazón, A
    Espinosa, JF
    Blanco-Urgoiti, J
    Schoepp, DD
    Wright, RA
    Johnson, BG
    Kingston, AE
    JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (17) : 3619 - 3629
  • [7] INVERSION OF CIS-SUBSTITUTED ALPHA-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 ANALOGS
    SHIMAMOTO, K
    OHFUNE, Y
    SYNLETT, 1993, (12) : 919 - 920
  • [8] Neurotoxicity of (2S,1'R,2'R,3'R)-2-(2,3-dicarboxycyclopropyl)glycine, a potent agonist for class II metabotropic glutamate receptors, in the rat
    Kwak, S
    Miyamoto, M
    Ishida, M
    Shinozaki, H
    NEUROSCIENCE, 1996, 73 (03) : 687 - 695
  • [9] Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist
    Pellicciari, R
    Marinozzi, M
    Natalini, B
    Costantino, G
    Luneia, R
    Giorgi, G
    Moroni, F
    Thomsen, C
    JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) : 2259 - 2269
  • [10] NOVEL METABOTROPIC GLUTAMATE-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
    EUROPEAN JOURNAL OF PHARMACOLOGY-MOLECULAR PHARMACOLOGY SECTION, 1994, 268 (02): : 267 - 270