dimethyl pyrrolidine-2,5-dicarboxylate | 90088-52-1

• 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: dimethyl pyrrolidine-2,5-dicarboxylate
• 英文别名: pyrrolidine-2,5-dicarboxylic acid dimethyl ester；Pyrrolidin-2,5-dicarbonsaeuredimethylester
• CAS: 90088-52-1；111071-93-3；115413-67-7；116836-62-5；116836-63-6
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: YGMCCBARPIHBKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl pyrrolidine-2,5-dicarboxylate 在 六甲基磷酰三胺 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 28.0h， 生成 1-O-benzyl 2-O,5-O-dimethyl 2-(2-chloroethyl)pyrrolidine-1,2,5-tricarboxylate
  参考文献：
  名称：

  N-金字塔形亚硝胺中可见光触发的一氧化氮释放

  摘要：

  虽然（phototriggered笼-NOS）已经被报道，释放一氧化氮（NO）在光照射许多有机/无机化合物，它们的光吸收波长大多位于紫外区，因为X  NO键（X =杂原子和金属）通常具有相当强大的π键性格。因此，本质上难以产生在可见光照射下释放NO的有机化合物。在此，描述了在可见光照射下释放NO的7-氮杂双环[2.2.1]庚烷的N-锥体亚硝胺衍生物的结构和性质。这些亚硝胺的吸收的红移，这归因于HOMO（N）-LUMO（π*）与N的非平面结构相关联的过渡NO部分使分子能够吸收可见光，从而导致NNO键断裂。因此，这些化合物是先天性有机笼状NO，不会被可见光束缚。

  DOI：

  10.1002/chem.201101427
• 作为产物：
  描述：

  二甲基2,5-二溴己二酸酯 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 40.0h， 生成 dimethyl pyrrolidine-2,5-dicarboxylate
  参考文献：
  名称：

  N-金字塔形亚硝胺中可见光触发的一氧化氮释放

  摘要：

  虽然（phototriggered笼-NOS）已经被报道，释放一氧化氮（NO）在光照射许多有机/无机化合物，它们的光吸收波长大多位于紫外区，因为X  NO键（X =杂原子和金属）通常具有相当强大的π键性格。因此，本质上难以产生在可见光照射下释放NO的有机化合物。在此，描述了在可见光照射下释放NO的7-氮杂双环[2.2.1]庚烷的N-锥体亚硝胺衍生物的结构和性质。这些亚硝胺的吸收的红移，这归因于HOMO（N）-LUMO（π*）与N的非平面结构相关联的过渡NO部分使分子能够吸收可见光，从而导致NNO键断裂。因此，这些化合物是先天性有机笼状NO，不会被可见光束缚。

  DOI：

  10.1002/chem.201101427

文献信息

• [EN] SPIRO-LACTAM AND BIS-SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS SPIRO-LACTAMES ET BIS-SPIRO-LACTAMES DES RÉCEPTEURS NMDA ET LEURS UTILISATIONS
  申请人：APTINYX INC

  公开号：WO2018026792A1

  公开（公告）日：2018-02-08

  Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  揭示了具有调节NMDA受体活性潜力的化合物。这些化合物可用于治疗
• [EN] SPIRO-LACTAM AND BIS-SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF<br/>[FR] SPIRO-LACTAME ET BIS-SPIRO-LACTAME MODULATEURS DES RÉCEPTEURS NMDA ET LEURS UTILISATIONS
  申请人：APTINYX INC

  公开号：WO2019152681A1

  公开（公告）日：2019-08-08

  Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

  披露了在调节NMDA受体活性方面具有潜力的化合物。这些化合物可用于治疗抑郁症及相关疾病以及其他疾病。
• Spiro-lactam and bis-spiro-lactam NMDA receptor modulators and uses thereof
  申请人：Aptinyx Inc.

  公开号：US11028095B2

  公开（公告）日：2021-06-08

  Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  所公开的化合物具有调节 NMDA 受体活性的功效。此类化合物可用于治疗抑郁症及相关疾病。此外，还公开了口服制剂和其他药学上可接受的化合物给药形式，包括静脉注射制剂。
• N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria
  作者：Lei Feng、Ke-Wu Yang、Li-Sheng Zhou、Jian-Min Xiao、Xia Yang、Le Zhai、Yi-Lin Zhang、Michael W. Crowder

  DOI：10.1016/j.bmcl.2012.06.074

  日期：2012.8

  In an effort to identify novel, broad-spectrum inhibitors against the metallo-beta-lactamases (M beta Ls), several N-heterocyclic derivatives were tested as inhibitors of M beta Ls CcrA, ImiS, and L1, which are representative enzymes from the distinct M beta L subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K-i values <= 2 mu M, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K-i values <7 mu M; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested M beta Ls. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4-thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MbLs. (c) 2012 Elsevier Ltd. All rights reserved.
• EP0873519A4
  申请人：——

  公开号：EP0873519A4

  公开（公告）日：2005-04-27