2-methyl-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine | 633305-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 2-methyl-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 3-(benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine
• CAS: 633305-10-9
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: UQFUYRZGLDEYTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 、 二甲氨基氯乙烷盐酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到N,N-dimethyl-N-{2-[2-methyl-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethyl}amine
  参考文献：
  名称：

  Novel 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines are potent 5-HT6 agonists

  摘要：

  A series of 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines 10a-z was prepared as novel 5-HT6 ligands. The best compounds were high affinity, full agonists at 5-HT6 receptors. Several agonists demonstrated good selectivity over other serotonergic and dopaminergic receptors. Acute administration of selective agonist 10e significantly increased extracellular GABA concentrations in rat frontal cortex. This compound also reduced adjunctive drinking behavior in the rat schedule-induced polydipsia assay, possibly predictive of efficacy in obsessive compulsive disorder and other anxiety related disorders. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.055
• 作为产物：
  描述：

  2-methyl-3-(phenylthio)-1H-pyrrolo[2,3-b]pyridine 在 Oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以32%的产率得到2-methyl-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Novel 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines are potent 5-HT6 agonists

  摘要：

  A series of 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines 10a-z was prepared as novel 5-HT6 ligands. The best compounds were high affinity, full agonists at 5-HT6 receptors. Several agonists demonstrated good selectivity over other serotonergic and dopaminergic receptors. Acute administration of selective agonist 10e significantly increased extracellular GABA concentrations in rat frontal cortex. This compound also reduced adjunctive drinking behavior in the rat schedule-induced polydipsia assay, possibly predictive of efficacy in obsessive compulsive disorder and other anxiety related disorders. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.055