benzyl 4-(5-tert-butoxycarbonylaminopent-1-yn-1-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate | 1360804-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-(5-tert-butoxycarbonylaminopent-1-yn-1-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate
• CAS: 1360804-75-6
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: KMXSWVHSOFDCCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-(5-tert-butoxycarbonylaminopent-1-yn-1-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate 在 盐酸 、 platinum(IV) oxide 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 水 、 乙腈 为溶剂， 20.0~110.0 ℃ 、448.17 kPa 条件下， 反应 1.0h， 生成 4-[4-(5-aminopentyl)piperidinyl]-1-o-tolylbutanone hydrochloride
  参考文献：
  名称：

  Fluorescent Derivatives of AC-42 To Probe Bitopic Orthosteric/Allosteric Binding Mechanisms on Muscarinic M1 Receptors

  摘要：

  Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor) prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [H-3]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.

  DOI：

  10.1021/jm201348t
• 作为产物：
  描述：

  4-哌啶酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 11.33h， 生成 benzyl 4-(5-tert-butoxycarbonylaminopent-1-yn-1-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate
  参考文献：
  名称：

  Fluorescent Derivatives of AC-42 To Probe Bitopic Orthosteric/Allosteric Binding Mechanisms on Muscarinic M1 Receptors

  摘要：

  Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor) prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [H-3]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.

  DOI：

  10.1021/jm201348t