(E)-1-<(tert-butoxycarbonyl)amino>-3-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>cyclobutane-1-carboxylic acid | 227453-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (E)-1-<(tert-butoxycarbonyl)amino>-3-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>cyclobutane-1-carboxylic acid
• CAS: 227453-86-3
• 化学式: C₁₂H₁₇N₃O₇
• 分子量: 315.283
• InChiKey: BBAWDJRIOMOCTN-KEYALVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  143.63
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-1-<(tert-butoxycarbonyl)amino>-3-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>cyclobutane-1-carboxylic acid 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到(E)-1-amino-3-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>cyclobutane-1-carboxylic acid hydrochloride
  参考文献：
  名称：

  Cyclobutane Quisqualic Acid Analogues as Selective mGluR5a Metabotropic Glutamic Acid Receptor Ligands

  摘要：

  The conformationally constrained cyclobutane analogues of quisqualic acid (Z)- and (E)-1-amino-3-[2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)]cyclobutane-1-carboxylic acid, compounds 2 and 3, respectively, were synthesized. Both 2 and 3 stimulated phosphoinositide (PI) hydrolysis in the hippocampus with EC50 values of 18 +/- 6 and 53 +/- 19 mu M, respectively. Neither analogue stimulated PI hydrolysis in the cerebellum. The effects of 2 and 3 were also examined in BHK cells which expressed either mGluR1a or mGluR5a receptors. Compounds 2 and 3 stimulated PI hydrolysis in cells expressing mGluR5a but not in those cells expressing mGluR1a. The EC50 value for 2 was 11 +/- 4 mu M, while that for 3 was 49 +/- 25 mu M. Both 2 and 3 did not show any significant effect on cells expressing the mGluR2 and mGluR4a receptors. In addition, neither compound blocked [H-3]glutamic acid uptake into synaptosomal membranes, and neither compound was able to produce the QUIS effect as does quisqualic acid. This pharmacological profile indicates that 2 and 3 are selective ligands for the mGluR5a metabotropic glutamic acid receptor.

  DOI：

  10.1021/jm9806897
• 作为产物：
  描述：

  (E)-ethyl 1-<(tert-butoxycarbonyl)amino>-3-<(benzyloxy)amino>cyclobutane-1-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 6.25h， 生成 (E)-1-<(tert-butoxycarbonyl)amino>-3-<2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)>cyclobutane-1-carboxylic acid
  参考文献：
  名称：

  Cyclobutane Quisqualic Acid Analogues as Selective mGluR5a Metabotropic Glutamic Acid Receptor Ligands

  摘要：

  The conformationally constrained cyclobutane analogues of quisqualic acid (Z)- and (E)-1-amino-3-[2'-(3',5'-dioxo-1',2',4'-oxadiazolidinyl)]cyclobutane-1-carboxylic acid, compounds 2 and 3, respectively, were synthesized. Both 2 and 3 stimulated phosphoinositide (PI) hydrolysis in the hippocampus with EC50 values of 18 +/- 6 and 53 +/- 19 mu M, respectively. Neither analogue stimulated PI hydrolysis in the cerebellum. The effects of 2 and 3 were also examined in BHK cells which expressed either mGluR1a or mGluR5a receptors. Compounds 2 and 3 stimulated PI hydrolysis in cells expressing mGluR5a but not in those cells expressing mGluR1a. The EC50 value for 2 was 11 +/- 4 mu M, while that for 3 was 49 +/- 25 mu M. Both 2 and 3 did not show any significant effect on cells expressing the mGluR2 and mGluR4a receptors. In addition, neither compound blocked [H-3]glutamic acid uptake into synaptosomal membranes, and neither compound was able to produce the QUIS effect as does quisqualic acid. This pharmacological profile indicates that 2 and 3 are selective ligands for the mGluR5a metabotropic glutamic acid receptor.

  DOI：

  10.1021/jm9806897