9-(4-hydroxybut-1-yl)-2-phenethoxyadenine | 1175565-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(4-hydroxybut-1-yl)-2-phenethoxyadenine
• 英文别名: 4-[6-Amino-2-(2-phenylethoxy)purin-9-yl]butan-1-ol
• CAS: 1175565-53-3
• 化学式: C₁₇H₂₁N₅O₂
• 分子量: 327.386
• InChiKey: IDKGOIBJUOIQKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(4-hydroxybut-1-yl)-2-phenethoxyadenine 在 磷酸三甲酯 、 三氯氧磷 、 水 作用下， 反应 3.0h， 生成 4-[6-Amino-2-(2-phenylethoxy)purin-9-yl]butyl dihydrogen phosphate
  参考文献：
  名称：

  Adenine-Based Acyclic Nucleotides as Novel P2X₃ Receptor Ligands

  摘要：

  A new series of acyclic nucleotides based on the adenine skeleton and bearing in 9-position a phosphorylated four carbon chain has been synthesized. Various substituents were introduced in 2-position of the adenine core. The new compounds were evaluated on rat P2X(3) receptors, using patch clamp recording from HEK transfected cells and the full P2X(3) agonist alpha,beta-meATP as reference compound. The results suggest that certain acyclic nucleotides, in particular compounds 28 and 29, are endowed with modest partial agonism on P2X(3) receptors. This is an interesting property that call depress the function of P2X(3) receptors, whose activation is believed to be involved in a number of chronic pain conditions including neuropathic pain and migraine. In fact, the new acyclic nucleotides are able to persistently block (by desensitization) P2X(3) receptor activity after a brief, modest activation, yet leaving the ability of sensory neurons to mediate responses to standard painful stimuli via a lower level of signaling.

  DOI：

  10.1021/jm900131v
• 作为产物：
  描述：

  苯乙醇 、 4-(6-amino-2-chloropurin-9-yl)butan-1-ol 在 sodium hydroxide 作用下， 反应 6.0h， 以79%的产率得到9-(4-hydroxybut-1-yl)-2-phenethoxyadenine
  参考文献：
  名称：

  Adenine-Based Acyclic Nucleotides as Novel P2X₃ Receptor Ligands

  摘要：

  A new series of acyclic nucleotides based on the adenine skeleton and bearing in 9-position a phosphorylated four carbon chain has been synthesized. Various substituents were introduced in 2-position of the adenine core. The new compounds were evaluated on rat P2X(3) receptors, using patch clamp recording from HEK transfected cells and the full P2X(3) agonist alpha,beta-meATP as reference compound. The results suggest that certain acyclic nucleotides, in particular compounds 28 and 29, are endowed with modest partial agonism on P2X(3) receptors. This is an interesting property that call depress the function of P2X(3) receptors, whose activation is believed to be involved in a number of chronic pain conditions including neuropathic pain and migraine. In fact, the new acyclic nucleotides are able to persistently block (by desensitization) P2X(3) receptor activity after a brief, modest activation, yet leaving the ability of sensory neurons to mediate responses to standard painful stimuli via a lower level of signaling.

  DOI：

  10.1021/jm900131v

文献信息

• Adenine-Based Acyclic Nucleotides as Novel P2X₃ Receptor Ligands
  作者：Rosaria Volpini、Ram Chandra Mishra、Dhuldeo D. Kachare、Diego Dal Ben、Catia Lambertucci、Ippolito Antonini、Sauro Vittori、Gabriella Marucci、Elena Sokolova、Andrea Nistri、Gloria Cristalli

  DOI：10.1021/jm900131v

  日期：2009.8.13

  A new series of acyclic nucleotides based on the adenine skeleton and bearing in 9-position a phosphorylated four carbon chain has been synthesized. Various substituents were introduced in 2-position of the adenine core. The new compounds were evaluated on rat P2X(3) receptors, using patch clamp recording from HEK transfected cells and the full P2X(3) agonist alpha,beta-meATP as reference compound. The results suggest that certain acyclic nucleotides, in particular compounds 28 and 29, are endowed with modest partial agonism on P2X(3) receptors. This is an interesting property that call depress the function of P2X(3) receptors, whose activation is believed to be involved in a number of chronic pain conditions including neuropathic pain and migraine. In fact, the new acyclic nucleotides are able to persistently block (by desensitization) P2X(3) receptor activity after a brief, modest activation, yet leaving the ability of sensory neurons to mediate responses to standard painful stimuli via a lower level of signaling.