3-(3,4-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine | 1492681-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(3,4-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
• CAS: 1492681-05-6
• 化学式: C₂₉H₂₆N₂O₆S
• 分子量: 530.601
• InChiKey: HPUMLSNOAGTTDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.88
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 在 水 、 三溴化硼 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-(3,4-dihydroxyphenyl)-5-(2,4-dihydroxyphenyl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Development of DANDYs, New 3,5-Diaryl-7-azaindoles Demonstrating Potent DYRK1A Kinase Inhibitory Activity

  摘要：

  A series of 3,5-diaryl-1H-pyrrolo[2,3-b]pyridines were synthesized and evaluated for inhibition of DYRKIA kinase in vitro. Derivatives having hydroxy groups on the aryl moieties (2c, 2j-l) demonstrated high inhibitory potencies with K(i)s in the low nanomolar range. Their methoxy analogues were up to 100 times less active. Docking studies at the ATP binding site suggested that these compounds bind tightly to this site via a network of multiple H-bonds with the peptide backbone. None of the active compounds were cytotoxic to KB cells at 10(-6) M. Kinase profiling revealed that compound 2j showed 2-fold selectivity for DYRK1A with respect to DYRK2 and DYRK3.

  DOI：

  10.1021/jm401049v
• 作为产物：
  描述：

  5-溴-3-碘-7-氮杂吲哚 在 四(三苯基膦)钯 、 苄基三乙基氯化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 mineral oil 为溶剂， 反应 7.0h， 生成 3-(3,4-dimethoxyphenyl)-5-(2,4-dimethoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine
  参考文献：
  名称：

  Development of DANDYs, New 3,5-Diaryl-7-azaindoles Demonstrating Potent DYRK1A Kinase Inhibitory Activity

  摘要：

  A series of 3,5-diaryl-1H-pyrrolo[2,3-b]pyridines were synthesized and evaluated for inhibition of DYRKIA kinase in vitro. Derivatives having hydroxy groups on the aryl moieties (2c, 2j-l) demonstrated high inhibitory potencies with K(i)s in the low nanomolar range. Their methoxy analogues were up to 100 times less active. Docking studies at the ATP binding site suggested that these compounds bind tightly to this site via a network of multiple H-bonds with the peptide backbone. None of the active compounds were cytotoxic to KB cells at 10(-6) M. Kinase profiling revealed that compound 2j showed 2-fold selectivity for DYRK1A with respect to DYRK2 and DYRK3.

  DOI：

  10.1021/jm401049v