1-(2-methoxybenzyl)-4,4'-bipiperidine | 383859-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(2-methoxybenzyl)-4,4'-bipiperidine
• 英文别名: 1-(2-Methoxy-benzyl)-[4,4'']bipiperidinyl；1-[(2-methoxyphenyl)methyl]-4-piperidin-4-ylpiperidine
• CAS: 383859-24-3
• 化学式: C₁₈H₂₈N₂O
• 分子量: 288.433
• InChiKey: FRRZPZBBNJYGBE-UHFFFAOYSA-N

物化性质

• 沸点：
  394.0±42.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  辛二酸 、 1-(2-methoxybenzyl)-4,4'-bipiperidine 在 氯甲酸乙酯 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 pipertramine amide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Methoctramine-Related Polyamines as Putative G_i Protein Activators

  摘要：

  The universal template approach provided a prospect of modifying methoctramine (2) structure. Thus, polyamines 3-7 were designed in which the flexibility of the diamino-hexane spacer of 2 was replaced by a bipiperidinyl moiety. In electrically stimulated guinea pig left atria, these novel polyamines, unlike prototype 2, displayed a potent intrinsic activity, which was in contrast with the muscarinic antagonism shown in binding studies by some of them (3 and 4) and was inhibited by benzalkonium chloride, an inhibitor of G(i) proteins.

  DOI：

  10.1021/jm0155594
• 作为产物：
  描述：

  N-boc-4,4-联哌啶 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(2-methoxybenzyl)-4,4'-bipiperidine
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Methoctramine-Related Polyamines as Putative G_i Protein Activators

  摘要：

  The universal template approach provided a prospect of modifying methoctramine (2) structure. Thus, polyamines 3-7 were designed in which the flexibility of the diamino-hexane spacer of 2 was replaced by a bipiperidinyl moiety. In electrically stimulated guinea pig left atria, these novel polyamines, unlike prototype 2, displayed a potent intrinsic activity, which was in contrast with the muscarinic antagonism shown in binding studies by some of them (3 and 4) and was inhibited by benzalkonium chloride, an inhibitor of G(i) proteins.

  DOI：

  10.1021/jm0155594

文献信息

• Synthesis of Monomeric Derivatives To Probe Memoquin’s Bivalent Interactions
  作者：Maria Laura Bolognesi、GianPaolo Chiriano、Manuela Bartolini、Francesca Mancini、Giovanni Bottegoni、Valentina Maestri、Stefan Czvitkovich、Manfred Windisch、Andrea Cavalli、Anna Minarini、Michela Rosini、Vincenzo Tumiatti、Vincenza Andrisano、Carlo Melchiorre

  DOI：10.1021/jm200691d

  日期：2011.12.22

  Eight monomeric congeners, related to the multitarget lead candidate memoquin, were prepared and evaluated at multiple targets to determine their profile against Alzheimer's disease. 2-4 bind to AChE with similar low nanomolar affinities and function as effective inhibitors of amyloid aggregation. The most potent monovalent ligand 2 also inhibits BACE-1 in vitro and APP metabolism in primary chicken telencephalic neurons.
• Design, Synthesis, and Biological Activity of Methoctramine-Related Polyamines as Putative G_i Protein Activators
  作者：Carlo Melchiorre、Maria L. Bolognesi、Roberta Budriesi、Carla Ghelardini、Alberto Chiarini、Anna Minarini、Michela Rosini、Vincenzo Tumiatti、Erik J. Wade

  DOI：10.1021/jm0155594

  日期：2001.11.1

  The universal template approach provided a prospect of modifying methoctramine (2) structure. Thus, polyamines 3-7 were designed in which the flexibility of the diamino-hexane spacer of 2 was replaced by a bipiperidinyl moiety. In electrically stimulated guinea pig left atria, these novel polyamines, unlike prototype 2, displayed a potent intrinsic activity, which was in contrast with the muscarinic antagonism shown in binding studies by some of them (3 and 4) and was inhibited by benzalkonium chloride, an inhibitor of G(i) proteins.