2-methyl-3-(phenylthio)-1H-pyrrolo[2,3-b]pyridine | 1186403-41-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-3-(phenylthio)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 2-methyl-3-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine
• CAS: 1186403-41-7
• 化学式: C₁₄H₁₂N₂S
• 分子量: 240.329
• InChiKey: OFNZIBAONIVUHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide 、 二苯二硫醚 在 碘 作用下， 反应 20.0h， 以91%的产率得到2-methyl-3-(phenylthio)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  由I2 / PEG-200促进的7-氮杂吲哚N-氧化物的区域选择性脱氧硫属元素化。

  摘要：

  我们为7-吲哚N-氧化物的区域选择性脱氧硫属元素化开发了一种通用且可持续的方法。内部氧化剂和绿色溶剂的组合已成功用于合成具有药用价值的单和二卤代羰基7-氮杂吲哚。区域选择性可通过反应条件的变化来调节。I 2 / PEG被建立为C–H硫属元素化的有效且可重复使用的催化系统。这种开发的方法具有广泛的底物范围，绿色反应条件和操作简便性，具有实际应用的巨大潜力。

  DOI：

  10.1039/c9ob02044f

文献信息

• Regioselective deoxygenative chalcogenation of 7-azindole <i>N</i>-oxides promoted by I₂/PEG-200
  作者：Shanshan Liu、Heng Yang、Lin-Yu Jiao、Jian-Hua Zhang、Chen Zhao、Yangmin Ma、Xiufang Yang

  DOI：10.1039/c9ob02044f

  日期：——

  deoxygenative chalcogenation of 7-azindole N-oxides; the combination of an internal oxidant and a green solvent has been used successfully for the synthesis of mono- and dichalcogenyl 7-azaindoles which are of pharmaceutical interest. The regioselectivity is tunable by the variation of the reaction conditions. I2/PEG was established as an efficient and reusable catalytic system for C–H chalcogenation. This

  我们为7-吲哚N-氧化物的区域选择性脱氧硫属元素化开发了一种通用且可持续的方法。内部氧化剂和绿色溶剂的组合已成功用于合成具有药用价值的单和二卤代羰基7-氮杂吲哚。区域选择性可通过反应条件的变化来调节。I 2 / PEG被建立为C–H硫属元素化的有效且可重复使用的催化系统。这种开发的方法具有广泛的底物范围，绿色反应条件和操作简便性，具有实际应用的巨大潜力。
• Novel 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines are potent 5-HT6 agonists
  作者：Ronald C. Bernotas、Steven Lenicek、Schuyler Antane、Derek C. Cole、Boyd L. Harrison、Albert J. Robichaud、Guo Ming Zhang、Deborah Smith、Brian Platt、Qian Lin、Ping Li、Joseph Coupet、Sharon Rosenzweig-Lipson、Chad E. Beyer、Lee E. Schechter

  DOI：10.1016/j.bmc.2009.05.055

  日期：2009.7

  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.