N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester | 130830-69-2

• 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
• 英文名称: N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester
• 英文别名: cis-N-(benzyloxycarbonyl)-4-carboxy-L-proline dimethyl ester；N-(benzyloxycarbonyl)-4-carboxy-L-proline dimethyl ester；(2S,4S)-1-benzyl 2,4-dimethyl pyrrolidine-1,2,4-tricarboxylate；1-O-benzyl 2-O,4-O-dimethyl (2S,4S)-pyrrolidine-1,2,4-tricarboxylate
• CAS: 130830-69-2
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: VFLKUGOZEYYCCP-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 cis-4-carboxy-L-proline dimethyl ester
  参考文献：
  名称：

  Conformationally defined neurotransmitter analogs. Selective inhibition of glutamate uptake by one pyrrolidine-2,4-dicarboxylate diastereomer

  摘要：

  In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared. These ''conformer mimics'', the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of [H-3]-L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites. While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport. These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.

  DOI：

  10.1021/jm00106a037
• 作为产物：
  描述：

  L-羟基脯氨酸 在 氯化亚砜 、 potassium carbonate 、 三乙胺 、 cesium fluoride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 N-(benzyloxycarbonyl)-cis-4-carboxy-L-proline dimethyl ester
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE
  [FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS POUR LEUR UTILISATION

  摘要：

  本发明涉及用于拮抗血管紧张素II型2（AT2）受体的杂环化合物。更具体地，本发明涉及吡咯烷和氮杂环丙烷化合物，含有它们的组合物以及它们在治疗或预防与AT2受体功能相关的疾病或疾病的方法中的使用，包括神经病性疼痛、炎症性疼痛、与神经元过敏、神经传导速度受损、细胞增殖紊乱、骨吸收和骨形成之间失衡以及与异常神经再生相关的疾病。

  公开号：

  WO2013102242A1

文献信息

• Pyrrolidine compounds
  申请人：Jiaang Weir-Torn

  公开号：US20070082932A1

  公开（公告）日：2007-04-12

  A compound of the following formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , T, X, Y, and Z are as defined herein. Also disclosed is a method for inhibiting dipeptidyl peptidase IV or for treating Type II diabetes with such a compound.

  以下化合物的公式：其中R1，R2，R3，R4，R5，R6，R7，R8，T，X，Y和Z的定义如本文所述。还公开了一种用这种化合物抑制二肽基肽酶IV或治疗II型糖尿病的方法。
• 2,7-substituted octahydro-pyrrolo 1,2-a]pyrazine derivatives as 5ht 1a ligands
  申请人：Pfizer Products Inc.

  公开号：EP0982030A2

  公开（公告）日：2000-03-01

  This invention relates to the use of compounds of formula I    wherein R1, R2, R3, X, m and n are defined as in the specification, and their pharmaceutically acceptable salts, for the treatment of disorders of the serotonin system.

  本发明涉及式 I 化合物的用途 其中 R1、R2、R3、X、m 和 n 的定义见说明书，以及它们的药学上可接受的盐类，用于治疗血清素系统紊乱。
• Proline–Glutamate Chimeras in Isopeptides. Synthesis and Biological Evaluation of Conformationally Restricted Glutathione Analogues
  作者：Mario Paglialunga Paradisi、Adriano Mollica、Ivana Cacciatore、Antonio Di Stefano、Francesco Pinnen、Anna Maria Caccuri、Giorgio Ricci、Silvestro Duprè、Alessandra Spirito、Gino Lucente

  DOI：10.1016/s0968-0896(03)00041-5

  日期：2003.4

  The two novel diastereoisomeric glutathione analogues I and 2 have been designed and synthesized by replacing the native gamma-glutamylic moiety with the conformational rigid skeleton of cis- or trans-4-carboxy-L-proline residue. Both analogues have been obtained by following the solution phase peptide chemistry methodologies and final reduction of the corresponding disulfide forms 13 and 14. The two analogues 1 and 2 have been tested towards gamma-glutamyltranspeptidase (gamma-GT) and human glutathione S-transferase (hGST P1-1). Both analogues 1 and 2 are completely resistant to enzymatic degradation by gamma-GT. The S-transferase utilizes the analogue 2 as a good substrate while is unable to bind the analogue 1. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 2,7-SUBSTITUTED OCTAHYDRO-PYRROLO 1,2-A]PYRAZINE DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0874849B1

  公开（公告）日：2001-09-19
• BRIDGES, RICHARD J.;STANLEY, MARK S.;ANDERSON, MICHAEL W.;COTMAN, CARL W.+, J. MED. CHEM., 34,(1991) N, C. 717-725
  作者：BRIDGES, RICHARD J.、STANLEY, MARK S.、ANDERSON, MICHAEL W.、COTMAN, CARL W.+

  DOI：——

  日期：——