tert-butyl 3-iodo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate | 1259851-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: tert-butyl 3-iodo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate
• 英文别名: tert-butyl 3-iodopyrazolo[4,3-b]pyridine-1-carboxylate
• CAS: 1259851-62-1
• 化学式: C₁₁H₁₂IN₃O₂
• 分子量: 345.14
• InChiKey: LTBXLCODFBGTHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硼-6-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]-1H-吲哚-1-羧酸-1-(1,1-二甲基乙基)酯 、 tert-butyl 3-iodo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 在 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 tert-butyl 3-(1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyl)oxy)-1H-indol-2-yl)-1H-pyrazolo[4,3-b]pyridine-1-carboxylate
  参考文献：
  名称：

  Optimisation of ITK inhibitors through successive iterative design cycles

  摘要：

  Based on a hit cluster of compounds inhibiting interleukin-2 inducible T-cell kinase (ITK) in the submicromolar range a series of ITK inhibitor libraries were synthesized. Through iterative design cycles including kinase crystal structure information, indolylindazole libraries were identified which showed low nanomolar activity in enzymatic and cellular assays. The potential of these novel lead series was confirmed through in vivo tests in an anti-CD3-IL2 mouse model. The intravenous administration of highly potent ITK inhibitor 11o resulted in dose-dependent, efficient suppression of IL-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.035
• 作为产物：
  描述：

  3-氟吡啶-2-醛 在 4-二甲氨基吡啶 、 碘 、 三乙胺 、 potassium hydroxide 、 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 tert-butyl 3-iodo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate
  参考文献：
  名称：

  Optimisation of ITK inhibitors through successive iterative design cycles

  摘要：

  Based on a hit cluster of compounds inhibiting interleukin-2 inducible T-cell kinase (ITK) in the submicromolar range a series of ITK inhibitor libraries were synthesized. Through iterative design cycles including kinase crystal structure information, indolylindazole libraries were identified which showed low nanomolar activity in enzymatic and cellular assays. The potential of these novel lead series was confirmed through in vivo tests in an anti-CD3-IL2 mouse model. The intravenous administration of highly potent ITK inhibitor 11o resulted in dose-dependent, efficient suppression of IL-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.035

文献信息

• Identification of potent ITK inhibitors through focused compound library design including structural information
  作者：Matthias Herdemann、Isabelle Heit、Frank-Uwe Bosch、Gianluca Quintini、Claudia Scheipers、Alexander Weber

  DOI：10.1016/j.bmcl.2010.09.119

  日期：2010.12

  A series of novel compound libraries inhibiting interleukin-2 inducible T cell kinase (ITK) were designed, synthesized and evaluated. In the first design cycle two library scaffolds were identified showing low micromolar inhibition of ITK. Further iterative design cycles including crystal structure information of ITK and structurally related kinases led to the identification of indolylindazole and indolylpyrazolopyridine compounds with low nanomolar ITK inhibition. (C) 2010 Elsevier Ltd. All rights reserved.