cis-1-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester | 121050-02-0

• 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-1-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester
• 英文别名: cis-dibenzyl 2,2'-(1-benzylazetidine-2,4-diyl)diacetate；dibenzyl cis-N-benzylazetidine-2,4-dicarboxylate；cis-N-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester；dibenzyl (2S,4R)-1-benzylazetidine-2,4-dicarboxylate
• CAS: 121050-02-0
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: HTSXADIWBSGYNM-PSWAGMNNSA-N

物化性质

• 沸点：
  539.8±50.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-1-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到((2R,4S)-1-benzylazetidine-2,4-diyl)dimethanol
  参考文献：
  名称：

  [EN] METHOD OF TREATMENT WITH 3-CYCLOPROPYLCARBONYL-3,6-DIAZABICYCLO[3.1.1]HEPTANE
  [FR] MÉTHODE DE TRAITEMENT PAR 3-CYCLOPROPYLCARBONYL-3,6-DIAZABICYCLO[3,1.1]HEPTANE

  摘要：

  本发明涉及3-环丙基甲酰基-3,6-二氮杂双环[3.1.1]庚烷，其盐形式，药物组合物和治疗方法。

  公开号：

  WO2014011863A1
• 作为产物：
  描述：

  α,α'-Dibromoglutaric anhydride 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 cis-1-benzylazetidine-2,4-dicarboxylic acid dibenzyl ester
  参考文献：
  名称：

  Synthesis and evaluation of novel azetidine analogs as potent inhibitors of vesicular [3H]dopamine uptake

  摘要：

  Lobelane analogs that incorporate a central piperidine or pyrrolidine moiety have previously been reported by our group as potent inhibitors of VMAT2 function. Further central ring size reduction of the piperidine moiety in lobelane to a four-membered heterocyclic ring has been carried out in the current study to afford novel cis-and trans-azetidine analogs. These azetidine analogs (15a-15c and 22a-22c) potently inhibited [H-3]dopamine (DA) uptake into isolated synaptic vesicles (K-i <= 66 nM). The cis-4-methoxy analog 22b was the most potent inhibitor (K-i = 24 nM), and was twofold more potent that either lobelane (2a, K-i = 45 nM) or norlobelane (2b, K-i = 43 nM). The trans-methylenedioxy analog, 15c (K-i = 31 nM), was equipotent with the cis-analog, 22b, in this assay. Thus, cis-and trans-azetidine analogs 22b and 15c represent potential leads in the discovery of new clinical candidates for the treatment of methamphetamine abuse. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.001

文献信息

• [EN] SALT FORMS OF 3 - CYCLOPROPYLCARBONYL - 3, 6 - DIAZABICYCLO [3.1.1] HEPTANE<br/>[FR] NOUVELLES FORMES SALINES DE 3-CYCLOPROPYLCARBONYL-3,6-DIAZABICYCLO[3.1.1]HEPTANE
  申请人：TARGACEPT INC

  公开号：WO2012125518A1

  公开（公告）日：2012-09-20

  The present invention relates to 3-cyclopropylcarbonyl-3,6-diazabicyclo[3.1.1]heptane, its salt forms, and novel polymorphic forms of these salts.

  本发明涉及3-环丙基甲酰基-3,6-二氮杂双环[3.1.1]庚烷，其盐形式，以及这些盐的新型多形式。
• [EN] METHOD OF TREATMENT WITH 3-CYCLOPROPYLCARBONYL-3,6-DIAZABICYCLO[3.1.1]HEPTANE<br/>[FR] MÉTHODE DE TRAITEMENT PAR 3-CYCLOPROPYLCARBONYL-3,6-DIAZABICYCLO[3,1.1]HEPTANE
  申请人：TARGACEPT INC

  公开号：WO2014011863A1

  公开（公告）日：2014-01-16

  The present invention relates to 3-cyclopropylcarbonyl-3,6-diazabicyclo[3.1.1]heptane, its salt forms, pharmaceutical compositions, and methods of treatment thereof.

  本发明涉及3-环丙基甲酰基-3,6-二氮杂双环[3.1.1]庚烷，其盐形式，药物组合物和治疗方法。
• 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。