cis-azetidine-2,4-dicarboxylic acid dimethyl ester | 127310-50-3

• 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: cis-azetidine-2,4-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl azetidine-cis-2,4-dicarboxylate；(2S,4R)-dimethyl azetidine-2,4-dicarboxylate；Azetidine-2,4-dicarboxylic acid dimethyl ester；dimethyl (2R,4S)-azetidine-2,4-dicarboxylate
• CAS: 127310-50-3
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: RYEDNANZSWYKTB-SYDPRGILSA-N

物化性质

• 沸点：
  238.6±40.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  cis-azetidine-2,4-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 锂硼氢 、 氢气 、 4-甲基苯磺酸吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 50.0 ℃ 、344.73 kPa 条件下， 反应 26.0h， 生成 (2S,4R)-1-(5-{2-[2-(2,2-Dimethyl-propionylamino)-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl]-ethyl}-thiophene-2-carbonyl)-4-(tetrahydro-pyran-2-yloxymethyl)-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Some Conformationally-constrained Glutamate Mimics of N-{5-[2-amino-3,4-dihydro-4-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-6-yl)ethyl]thien-2-ylcarbonyl-L-glutamic Acid (LY254155)

  摘要：

  DOI：

  10.3987/com-96-7608
• 作为产物：
  描述：

  2,4-二溴戊二酸二甲酯 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-azetidine-2,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis and bioactivity of a new class of rigid glutamate analogs. Modulators of the N-methyl-D-aspartate receptor

  摘要：

  A variety of derivatives of azetidine-2,4-dicarboxylic acid were synthesized and examined for their ability to stimulate 45Ca2+ uptake in cultures of cerebellar granule cells. Of the compounds tested, the cis-azetidine-2,4-dicarboxylic acid (10f) was found to be the most potent agent in potentiating glutamate, aspartate, or N-methyl-D-aspartate (NMDA) stimulated 45Ca2+ uptake at the NMDA receptor. The mechanism of action of 10f was further investigated in [3H]MK-801 binding assays and [3H]GABA release from cultured embryonic rat forebrain neurons. All of the results from the functional studies of azetidine 10f are consistent with a selectivity of action at the NMDA receptor. Moreover, azetidine 10f appears to exhibit a dual type of action, behaving as a glutamate-like agonist at higher concentrations and as a positive modulator at concentrations below 50 microM.

  DOI：

  10.1021/jm00168a007

文献信息

• Neurotrophic 2-azetidinecarboxylic acid derivatives, and related compositions and methods
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06544976B1

  公开（公告）日：2003-04-08

  This invention provides compounds having the following general structure: This invention also provides pharmaceutical compositions comprising same and methods of using these compositions to treat and prevent disorders characterized by neuronal damage.

  这项发明提供具有以下一般结构的化合物。这项发明还提供包含相同化合物的药物组合物，以及使用这些组合物来治疗和预防以神经元损伤为特征的疾病的方法。
• Azetidine derivatives, compositions and methods of treating
  申请人：Fidia-Georgetown Institute for the Neurosciences

  公开号：US04946839A1

  公开（公告）日：1990-08-07

  This invention relates to novel azetidines and derivative thereof, as well as to pharmaceutical compositions and methods of treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型的氮杂环丙烷及其衍生物，以及制备药物组合物和治疗记忆和学习障碍的方法。本发明的另一个方面涉及利用这些化合物和组合物作为生物学工具和材料，以表征兴奋性氨基酸受体系统的方法。本发明的另一个方面涉及治疗PCP毒性和滥用的方法。
• Azetidine derivatives to treat memory and learning disorders
  申请人：FIDIA-Georgetown Institute for the Neurosciences

  公开号：US04990504A1

  公开（公告）日：1991-02-05

  This invention relates to novel azetidines and derivatives thereof, as well as to pharmaceutical compositions and methods of treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型氮杂四环和其衍生物，以及制备药物组合物和治疗记忆和学习障碍的方法。本发明的另一个方面涉及利用这些化合物和组合物作为生物工具和材料，用于表征兴奋性氨基酸受体系统的方法。本发明的另一个方面涉及一种治疗PCP毒性和滥用的方法。
• Azetidine derivatives, compositions and their use
  申请人：FIDIA-GEORGETOWN INSTITUTE FOR THE NEUROSCIENCES

  公开号：EP0299513A1

  公开（公告）日：1989-01-18

  This invention relates to novel azetidines and derivatives thereof, as well as to pharmaceutical compositions and their use for treating memory and learning disorders. Another aspect of the invention relates to a method of utilizing the compounds and compositions as biological tools and materials for characterizing excitatory amino acid receptor systems. A further aspect of the invention relates to a method of treating PCP toxicity and abuse.

  本发明涉及新型氮杂环丁烷及其衍生物，以及药物组合物及其用于治疗记忆和学习障碍的用途。本发明的另一方面涉及一种利用这些化合物和组合物作为生物工具和材料来表征兴奋性氨基酸受体系统的方法。本发明的另一方面涉及一种治疗五氯苯酚毒性和滥用的方法。
• KOZIKOWSKI, ALAN P.;TUCKMANTEL, WERNER;REYNOLDS, IAN J.;WROBLEWSKI, JARDA+, J. MED. CHEM., 33,(1990) N, C. 1561-1571
  作者：KOZIKOWSKI, ALAN P.、TUCKMANTEL, WERNER、REYNOLDS, IAN J.、WROBLEWSKI, JARDA+

  DOI：——

  日期：——