(2R,4r)-1-苄基-4-氨基-吡咯烷-2,4-二羧酸 | 171336-76-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2R,4r)-1-苄基-4-氨基-吡咯烷-2,4-二羧酸
• 英文名称: (2R,4R) 4-amino-1-(benzyl)-pyrrolidine-2,4-dicarboxylic acid
• 英文别名: (2R,4R)-4-azaniumyl-1-benzylpyrrolidin-1-ium-2,4-dicarboxylate
• CAS: 171336-76-8
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: LYCSUAGKQMUTBR-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4r)-1-苄基-4-氨基-吡咯烷-2,4-二羧酸 在 palladium dihydroxide 盐酸 、 N-氯代丁二酰亚胺 、 氯化亚砜 、 titanium(III) chloride 、 苄基三乙基氯化铵 、 氨 、 氢气 、 碳酸氢钠 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 11.0h， 生成 1-amino-APDC
  参考文献：
  名称：

  1-amino-APDC, a partial agonist of group II metabotropic glutamate receptors with neuroprotective properties

  摘要：

  The synthesis of the 1-amino derivative of (2R,4R)-4-aminopyrrolidine-2,4-dicarboxylic acid (1-amino-APDC), a selective metabotropic glutamate ligand, is disclosed. This compound acts as a partial agonist of the group II mGluRs and shows pronounced neuroprotective properties in the NMDA model of cell toxicity, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00266-8
• 作为产物：
  描述：

  (2R)-ethyl N¹-benzyl-4-oxopyrrolidine-2-carboxylate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 (2R,4r)-1-苄基-4-氨基-吡咯烷-2,4-二羧酸
  参考文献：
  名称：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues

  摘要：

  Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.

  DOI：

  10.1016/0957-4166(95)00209-8

文献信息

• Synthesis and metabotropic glutamate receptor antagonist activity of N1-substituted analogs of 2R,4R-4-aminopyrrolidine-2,4-dicarboxylic acid
  作者：Matthew J Valli、Darryle D Schoepp、Rebecca A Wright、Bryan G Johnson、Ann E Kingston、Rosemarie Tomlinson、James A Monn

  DOI：10.1016/s0960-894x(98)00352-7

  日期：1998.8

  4R-APDC) has been prepared as constrained analogs of gamma-substituted glutamic acids and examined for their effects at recombinant metabotropic glutamate receptor (mGluR) subtypes in vitro. Appropriate substitution of the N1 position of 2R,4R-APDC resulted in the identification of a number of selective group II mGluR antagonists.

  制备了一系列（2R，4R）-4-氨基吡咯烷-2,4-二羧酸（2R，4R-APDC）的N1取代衍生物作为γ-取代谷氨酸的约束类似物，并研究了它们在重组代谢型中的作用体外谷氨酸受体（mGluR）亚型。适当替换2R，4R-APDC的N1位置导致鉴定出许多选择性的II类mGluR拮抗剂。
• Pyrrolidinyl di-carboxylic acid derivatives as metabotropic glutamate receptor antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0703218A1

  公开（公告）日：1996-03-27

  The present invention provides pyrrolidinyl di-carboxylic acid derivatives that affect certain excitatory amino acid receptors, and are useful in the treatment of neurological disorders and psychiatric disorders. This invention further provides novel pyrrolidinyl di-carboxylic acid derivatives and pharmaceutical formulations employing these novel compounds.

  本发明提供了影响特定兴奋性氨基酸受体的吡咯烷二羧酸衍生物，并且在治疗神经系统疾病和精神疾病方面具有用途。本发明还提供了新型的吡咯烷二羧酸衍生物和使用这些新化合物的药物配方。
• Synthesis, molecular modeling, and biology of the 1-benzyl derivative of APDC-an apparent mGluR6 selective ligand
  作者：Werner Tückmantel、Alan P. Kozikowski、Shaomeng Wang、Sergey Pshenichkin、Jarda T. Wroblewski

  DOI：10.1016/s0960-894x(97)00068-1

  日期：1997.3

  The synthesis of the 1-benzyl derivative of (2R,4R)-4-aminopyrrolidine-2,4-dicarboxylic acid (1-benzyl-APDC) starting from cis-4-hydroxy-D-proline is disclosed together with a study of the activity of this compound at metabotropic glutamate receptors (mGluRs). The compound was found to display good mGluR6 selectivity, and may thus be a useful pharmacological research tool. (C) 1997 Elsevier Science Ltd. All rights reserved.
• US5473077A
  申请人：——

  公开号：US5473077A

  公开（公告）日：1995-12-05
• [EN] PYRROLIDINYL DI-CARBOXYLIC ACID DERIVATIVES AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE L'ACIDE PYRROLIDINYLDICARBOXYLIQUE ANTAGONISTES DES RECEPTEURS DU GLUTAMATE METABOTROPE
  申请人：ELI LILLY AND COMPANY

  公开号：WO1996005828A1

  公开（公告）日：1996-02-29

  (EN) The present invention provides pyrrolidinyl di-carboxylic acid derivatives that affect certain excitatory amino acid receptors, and are useful in the treatment of neurological disorders and psychiatric disorders. This invention further provides novel pyrrolidinyl di-carboxylic acid derivatives and pharmaceutical formulations employing these novel compounds.(FR) L'invention porte sur des dérivés de l'acide pyrrolidinyldicarboxylique affectant certains récepteurs d'acides aminés excitateurs et s'avérant utiles dans le traitement de troubles neurologiques et psychiatriques. L'invention porte également sur de nouveaux dérivés de l'acide pyrrolidinyldicarboxylique et sur des préparations pharmaceutiques les contenant.