cis-1-acetylazetidine-2,4-dicarboxylic acid | 121050-09-7

• 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-acetylazetidine-2,4-dicarboxylic acid
• 英文别名: cis-N-acetylazetidine-2,4-dicarboxylic acid；(2R,4S)-1-acetylazetidine-2,4-dicarboxylic acid
• CAS: 121050-09-7
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: YHOCGNVJQZRXBU-SYDPRGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-二溴戊二酸 在 palladium dihydroxide 吡啶 、 氢气 、 sodium hydride 、 对甲苯磺酸 、 苯甲醇 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 40.5h， 生成 cis-1-acetylazetidine-2,4-dicarboxylic acid
  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

• 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.

  本发明涉及新型的氮杂四元环及其衍生物，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将这些化合物和组合物作为生物学工具和材料用于表征兴奋性氨基酸受体系统的方法。本发明的进一步方面涉及一种治疗PCP中毒和滥用的方法。
• 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：——
• US4946839A
  申请人：——

  公开号：US4946839A

  公开（公告）日：1990-08-07
• US4990504A
  申请人：——

  公开号：US4990504A

  公开（公告）日：1991-02-05