3-phenyl-5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine | 875638-40-7

• 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: 3-phenyl-5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine
• 英文别名: 5-(3,4-dimethoxyphenyl)-3-phenyl-1H-pyrrolo[2,3-b]pyridine
• CAS: 875638-40-7
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: PTKRZXHHLCHSFE-UHFFFAOYSA-N

物化性质

• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以52%的产率得到3-phenyl-5-(3,4-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 、 水 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 、 mineral oil 为溶剂， 反应 7.0h， 生成 3-phenyl-5-(3,4-dimethoxyphenyl)-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

文献信息

• COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR
  申请人：Ibrahim Prabha N.

  公开号：US20120022098A1

  公开（公告）日：2012-01-26

  Compounds active on protein kinases are described, as well as methods of using such compounds to treat diseases and conditions associated with aberrant activity of protein kinases.

  本文描述了对蛋白激酶活性起作用的化合物，以及使用这些化合物治疗与蛋白激酶异常活性有关的疾病和病况的方法。
• PYRROLO-PYRIDINE KINASE MODULATORS
  申请人：Arnold William D.

  公开号：US20090005378A1

  公开（公告）日：2009-01-01

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂以及使用这些新型吡咯-吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。
• Pyrrolo-pyridine kinase modulators
  申请人：Arnold D. William

  公开号：US20070043068A1

  公开（公告）日：2007-02-22

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂及使用这些新型吡咯-吡啶激酶调节剂治疗通过激酶活性介导的疾病的方法。
• PYRROLO-PYRIDINE KINASE MODULATIORS
  申请人：Arnold William D.

  公开号：US20090143352A1

  公开（公告）日：2009-06-04

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂以及使用这些新型吡咯-吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。
• 3,5-DIPHENYL-SUBSTITUTED PYRROLO[2,3b]PYRIDINES USEFUL AS KINASE INHIBITORS
  申请人：SGX Pharmaceuticals, Inc.

  公开号：EP2264033A1

  公开（公告）日：2010-12-22

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity. wherein L1 and L2 are bonds; R1 is -C(O)NR14R15.

  本发明提供了新型吡咯并吡啶激酶调节剂和使用新型吡咯并吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。 其中 L1 和 L2 是键； R1 是-C(O)NR14R15。