| 1609464-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• CAS: 1609464-27-8
• 化学式: C₂₁H₂₅N₅O₃S
• 分子量: 427.527
• InChiKey: YEJWKNOKVJVXCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  80.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 以12 mg的产率得到2-(2-((pyridin-3-yloxy)methyl)piperazin-1-yl)thiazolo[4,5-b]pyridine hydrochloride
  参考文献：
  名称：

  Discovery of Novel 2-((Pyridin-3-yloxy)methyl)piperazines as α7 Nicotinic Acetylcholine Receptor Modulators for the Treatment of Inflammatory Disorders

  摘要：

  Herein we report the design, synthesis, and structure activity relationships for a new class of alpha 7 nicotinic acetylcholine receptor (nAChR) modulators based on the 2-((pyridin-3-yloxy)methyl)piperazine scaffold. The oxazolo[4,5-b]pyridine, (R)-18, and 4-methoxyphenylurea, (R)-47, were identified as potent and selective modulators of the alpha 7 nAChR with favorable in vitro safety profiles and good oral bioavailability in mouse. Both compounds were shown to significantly inhibit cellular infiltration in a murine model of allergic lung inflammation. Despite the structural and in vivo functional similarities in the compounds, only (R)-18 was shown to be an agonist. Compound (R)-47 demonstrated silent agonist activity. These data support the hypothesis that the anti-inflammatory activity of the alpha 7 nAChR is mediated by a signal transduction pathway that is independent of ion current.

  DOI：

  10.1021/jm5004599
• 作为产物：
  描述：

  3-氧代四氢-1H-噁唑并[3,4-a]吡嗪-7(3H)-羧酸叔丁酯 在 potassium tert-butylate 、 palladium diacetate 、 三苯基膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 120.5h， 生成
  参考文献：
  名称：

  Discovery of Novel 2-((Pyridin-3-yloxy)methyl)piperazines as α7 Nicotinic Acetylcholine Receptor Modulators for the Treatment of Inflammatory Disorders

  摘要：

  Herein we report the design, synthesis, and structure activity relationships for a new class of alpha 7 nicotinic acetylcholine receptor (nAChR) modulators based on the 2-((pyridin-3-yloxy)methyl)piperazine scaffold. The oxazolo[4,5-b]pyridine, (R)-18, and 4-methoxyphenylurea, (R)-47, were identified as potent and selective modulators of the alpha 7 nAChR with favorable in vitro safety profiles and good oral bioavailability in mouse. Both compounds were shown to significantly inhibit cellular infiltration in a murine model of allergic lung inflammation. Despite the structural and in vivo functional similarities in the compounds, only (R)-18 was shown to be an agonist. Compound (R)-47 demonstrated silent agonist activity. These data support the hypothesis that the anti-inflammatory activity of the alpha 7 nAChR is mediated by a signal transduction pathway that is independent of ion current.

  DOI：

  10.1021/jm5004599