1-(2-乙氧基-2-氧代乙基)3-吡咯烷甲酸甲酯 | 142483-57-6

• 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
• 中文名称: 1-(2-乙氧基-2-氧代乙基)3-吡咯烷甲酸甲酯
• 英文名称: 1-<(ethoxycarbonyl)methyl>-3-(methoxycarbonyl)pyrrolidine
• 英文别名: Methyl 1-(2-ethoxy-2-oxoethyl)pyrrolidine-3-carboxylate
• CAS: 142483-57-6
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: YEWLMKULNKTPIM-UHFFFAOYSA-N

物化性质

• 沸点：
  273℃
• 密度：
  1.124
• 闪点：
  119℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1-(2-乙氧基-2-氧代乙基)3-吡咯烷甲酸甲酯 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以36%的产率得到1-氮杂双环[2.2.1]庚烷-3-酮
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007
• 作为产物：
  描述：

  N-苄基吡咯烷-3-甲酸甲酯 、 溴乙酸乙酯 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 生成 1-(2-乙氧基-2-氧代乙基)3-吡咯烷甲酸甲酯
  参考文献：
  名称：

  Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands

  摘要：

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.

  DOI：

  10.1021/jm00091a007

文献信息

• Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them
  申请人：Beecham Group p.l.c.

  公开号：EP0402056A2

  公开（公告）日：1990-12-12

  A compound of formula (I) or a pharmaceutically acceptable salt thereof: in which one of X and Y represents hydrogen and the other represents Z, where Z is a group in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises two or three nitrogen atoms, any amino nitrogen being substituted by a C1-2 alkyl, cyclopropyl or propargyl group, r represents an integer of 2 or 3, s represents an integer of 1 or 2 and t represents 0 or 1, with the proviso that when Y is hydrogen s is 1.

  式 (I) 的化合物或其药学上可接受的盐： 其中 X 和 Y 的一个代表氢，另一个代表 Z，其中 Z 是一个基团 其中 Q 代表完成五元芳香环的三元二价残基，包含两个或三个氮原子，任何氨基氮均被 C1-2 烷基、环丙基或丙炔基取代，r 代表 2 或 3 的整数，s 代表 1 或 2 的整数，t 代表 0 或 1，但当 Y 为氢时，s 为 1。
• Azabicyclic Derivatives having muscarinic receptor affinity
  申请人：BEECHAM GROUP PLC

  公开号：EP0414394A2

  公开（公告）日：1991-02-27

  A pharmaceutical composition which comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof: in which p is 1 and either m is 0 and n is 2 or 3 or m is 1 and n is 2, or p is 2, m is 0 and n is 2, and Z is a heterocyclic group in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, or three nitrogen atoms, any amino nitrogen being substituted by a C₁₋₂ alkyl, cyclopropyl or propargyl group, and any ring carbon atom being optionally substituted by a group R₁; or a group in which A₁, A₂ and A₃ complete a 5-membered aromatic ring and A₁ is oxygen or sulphur, one of A₂ and A₃ is CR₂ and the other is nitrogen or CR₃, or A₂ is oxygen or sulphur, one of A₁ and A₃ is CR₂ and the other is CR₃; and R₁, R₂ and R₃ are independently selected from hydrogen, halogen, N(R₄)₂, C₂₋₃ alkenyl, C₂₋₃ alkynyl or C₁₋₂ alkyl optionally substituted with one, two or three fluorine atoms, in which each R₄ is independently hydrogen or methyl, and a pharmaceutically acceptable carrier.

  一种药物组合物，包含式 (I) 的化合物或其药学上可接受的盐： 其中 p 为 1，m 为 0，n 为 2 或 3，或 m 为 1，n 为 2，或 p 为 2，m 为 0，n 为 2，Z 为杂环基团 其中 Q 代表完成 5 元芳香环的 3 元二价残基，包含 1 个或 2 个选自氧、氮和硫的杂原子，或 3 个氮原子，任何氨基氮被 C₁₋₂烷基、环丙基或丙炔基取代，任何环碳原子任选被基团 R₁ 取代；或一个基团 其中 A₁、A₂ 和 A₃ 构成一个 5 元芳香环，且 A₁ 为氧或硫、A₂ 和 A₃ 中的一个是 CR₂，另一个是氮或 CR₃，或者 A₂ 是氧或硫，A₁ 和 A₃ 中的一个是 CR₂，另一个是 CR₃；且 R₁、R₂ 和 R₃ 独立选自氢、卤素、N(R₄)₂、C₂₋₃ 烯基、C₂₋₃ 炔基或任选被一个取代的 C₁₋₂ 烷基、其中每个 R₄ 独立地为氢或甲基，以及药学上可接受的载体。
• US5217975A
  申请人：——

  公开号：US5217975A

  公开（公告）日：1993-06-08
• US5470859A
  申请人：——

  公开号：US5470859A

  公开（公告）日：1995-11-28
• Substituent variation in azabicyclic triazole- and tetrazole-based muscarinic receptor ligands
  作者：Sarah M. Jenkins、Harry J. Wadsworth、Steven Bromidge、Barry S. Orlek、Paul A. Wyman、Graham J. Riley、Julie Hawkins

  DOI：10.1021/jm00091a007

  日期：1992.6

  The effect of variation of the 1-azabicyclic substituent on the novel 1,2,3-triazol-4-yl-, 1,2,4-triazol-1-yl-, tetrazol-5-yl-, and tetrazol-2-yl-based muscarinic receptor ligands ha, been studied, and the exo-azabicyclic[2.2.1]hept-3-yl substituent was found to give the most potent and efficacious compounds. In addition, variation of the second substituent on 1,2,4-triazol-1-yl- and tetrazol-2-yl-based muscarinic receptor ligands has yielded a series of novel compounds with high potencies and efficacies, ranging from full agonists to antagonists. Small lipophilic electron withdrawing substituents give potent but low efficacy compounds, while small polar electron donating substituents give potent and efficacious compounds. The activity of these compounds is described in terms of a model of the receptor involving lipophilic and hydrogen bonding interactions. These compounds provide muscarinic ligands with high potency and a range of efficacies suitable for testing as candidate drugs in the treatment of Alzheimer's disease.