4-hydroxy-2-pyridin-2-ylmethyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ylium chloride hydrochloride | 947408-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-hydroxy-2-pyridin-2-ylmethyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ylium chloride hydrochloride
• 英文别名: 4-hydroxy-2-(pyridin-1-ium-2-ylmethyl)-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ium dichloride；4-Hydroxy-2-(pyridin-1-ium-2-ylmethyl)-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ium dichloride；2-(pyridin-1-ium-2-ylmethyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazin-5-ium-4-ol;dichloride
• CAS: 947408-20-0
• 化学式: C₁₄H₁₆N₃O*ClH*Cl
• 分子量: 314.214
• InChiKey: BTGIPRYLBDXTOB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-2-pyridin-2-ylmethyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ylium chloride hydrochloride 在 四甲基胍 作用下， 以 氘代甲醇 为溶剂， 生成 2-[Bis(pyridin-2-ylmethyl)amino]acetaldehyde
  参考文献：
  名称：

  A Reversible pH-Dependent Intramolecular Pyridine−Aldehyde Cyclization

  摘要：

  [GRAPHICS]A dipicolylamine (DPA) attached to an aldehyde moiety cyclizes to form a pyridinium-fused heterocycle. This intramolecular reaction between the pyridine and aldehyde moieties is reversible, and the position of the equilibrium is controlled by pH. The fused-ring heterocycle is stabilized under acidic conditions, whereas the ring-opened form is the major species under basic conditions. The ring-closed form can be utilized as a masked aldehyde precursor to access a variety of functional metal chelators containing the DPA unit.

  DOI：

  10.1021/jo702394v
• 作为产物：
  描述：

  2,2-dimethoxy-N,N-bis(pyridin-2-ylmethyl)ethanamine 在 盐酸 作用下， 反应 5.0h， 生成 4-hydroxy-2-pyridin-2-ylmethyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrazin-5-ylium chloride hydrochloride
  参考文献：
  名称：

  A Reversible pH-Dependent Intramolecular Pyridine−Aldehyde Cyclization

  摘要：

  [GRAPHICS]A dipicolylamine (DPA) attached to an aldehyde moiety cyclizes to form a pyridinium-fused heterocycle. This intramolecular reaction between the pyridine and aldehyde moieties is reversible, and the position of the equilibrium is controlled by pH. The fused-ring heterocycle is stabilized under acidic conditions, whereas the ring-opened form is the major species under basic conditions. The ring-closed form can be utilized as a masked aldehyde precursor to access a variety of functional metal chelators containing the DPA unit.

  DOI：

  10.1021/jo702394v

文献信息

• USE OF CHELATORS OF DIVALENT CATIONS TO PROMOTE NERVE REGENERATION
  申请人：MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：US20140179741A1

  公开（公告）日：2014-06-26

  Disclosed herein are methods to promote axonal outgrowth of a neuron comprising, contacting the neuron with an effective amount of a chelating agent, to thereby promote axonal outgrowth in the neuron. Also disclosed are methods of treating a subject for a CNS lesion, comprising, administering to the subject a therapeutically effective amount of a chelating agent, Also disclosed are devices for promoting regeneration in a lesioned neuron, and pharmaceutical compositions comprising a therapeutically effective amount of a chelating agent formulated for localized administration directly to an injured neuron. Examples of such chelating agents are provided.

  本文揭示了一种促进神经元轴突生长的方法，包括将有效量的螯合剂与神经元接触，从而促进神经元的轴突生长。还揭示了治疗中枢神经系统损伤的方法，包括向受试者施用治疗有效量的螯合剂。还揭示了促进受损神经元再生的装置和制剂，其中包括经局部给药制备的治疗有效量的螯合剂。提供了这种螯合剂的示例。
• A Reversible pH-Dependent Intramolecular Pyridine−Aldehyde Cyclization
  作者：Xiao-an Zhang、Datong Song、Stephen J. Lippard

  DOI：10.1021/jo702394v

  日期：2008.1.1

  [GRAPHICS]A dipicolylamine (DPA) attached to an aldehyde moiety cyclizes to form a pyridinium-fused heterocycle. This intramolecular reaction between the pyridine and aldehyde moieties is reversible, and the position of the equilibrium is controlled by pH. The fused-ring heterocycle is stabilized under acidic conditions, whereas the ring-opened form is the major species under basic conditions. The ring-closed form can be utilized as a masked aldehyde precursor to access a variety of functional metal chelators containing the DPA unit.