4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoic acid | 1226854-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoic acid
• CAS: 1226854-16-5
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: IGYFNWOGGJYLIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-氧杂-3-氮杂双环[3,2,1]辛烷 、 4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoic acid 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到1-methyl-4-[4-(8-oxa-3-azabicyclo[3.2.1]octane-3-carbonyl)phenyl]-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
  参考文献：
  名称：

  Discovery and optimization of 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

  摘要：

  Wediscovered 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR). Since phenolic OH groups pose metabolic liability, one of the two hydroxyl groups was selectively removed. The SAR data showed the structural features necessary for subnanomolar inhibitory activity against mTOR kinase as well as selectivity over PI3K alpha. An X-ray co-crystal structure of one inhibitor with the mTOR-related PI3K gamma revealed the key hydrogen bonding interactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.135
• 作为产物：
  描述：

  methyl 4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以80%的产率得到4-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoic acid
  参考文献：
  名称：

  Discovery and optimization of 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

  摘要：

  Wediscovered 2-(4-substituted-pyrrolo[2,3-b]pyridin-3-yl)methylene-4-hydroxybenzofuran-3(2H)-ones as potent and selective ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR). Since phenolic OH groups pose metabolic liability, one of the two hydroxyl groups was selectively removed. The SAR data showed the structural features necessary for subnanomolar inhibitory activity against mTOR kinase as well as selectivity over PI3K alpha. An X-ray co-crystal structure of one inhibitor with the mTOR-related PI3K gamma revealed the key hydrogen bonding interactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.135