3-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol | 784150-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol
• CAS: 784150-43-2
• 化学式: C₁₂H₈BrN₃O₂
• 分子量: 306.118
• InChiKey: PINOWBSNJVHVII-UHFFFAOYSA-N

物化性质

• 密度：
  1.764±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol 、 3-氨基苯硼酸 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以56%的产率得到3-[[6-(3-氨基苯基)-7H-吡咯并[2,3-d]嘧啶-4-基]氧基]苯酚
  参考文献：
  名称：

  Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: a novel route to TWS119, a glycogen synthase kinase-3β inhibitor

  摘要：

  A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3 beta inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.032
• 作为产物：
  描述：

  6-溴-4-氯-7H-吡咯并嘧啶 、 间苯二酚 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以8%的产率得到3-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenol
  参考文献：
  名称：

  Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: a novel route to TWS119, a glycogen synthase kinase-3β inhibitor

  摘要：

  A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3 beta inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.032

文献信息

• Compounds that induce neuronal differentiation in embryonic stem cells
  申请人：Ding Sheng

  公开号：US20050038049A1

  公开（公告）日：2005-02-17

  The invention provides a novel class of compounds and compositions that are useful in the treatment or prevention of diseases or disorders associated with kinases, particularly GSK-3β, c-Abl, HER-1, HER-2, KDR, Flt-3, c-Raf-1, PDGFR-β, c-Kit, Flt-4, Flt-1, Tek, c-src, CDK1, PDK1, FGFR-1, FGFR-2, Fer, MAP3K13, EPHA7 and c-Met kinases. The invention further relates to the use of the compounds of the invention as potent inducers of neurogenesis in embryonic stem cells.

  本发明提供了一类新型化合物和组合物，可用于治疗或预防与激酶有关的疾病或疾病，特别是GSK-3β，c-Abl，HER-1，HER-2，KDR，Flt-3，c-Raf-1，PDGFR-β，c-Kit，Flt-4，Flt-1，Tek，c-src，CDK1，PDK1，FGFR-1，FGFR-2，Fer，MAP3K13，EPHA7和c-Met激酶相关的疾病或疾病。本发明进一步涉及使用本发明的化合物作为胚胎干细胞中神经元发生的强效诱导剂。
• 6-phenyl-7H-pyrrolo[2,3-d]pyrimidine compounds that induce neuronal differentiation in embryonic stem cells
  申请人：IRM LLC

  公开号：US07253166B2

  公开（公告）日：2007-08-07

  The invention provides a novel class of compounds and compositions of Formula I: in which R1, R2 and R3 are defined herein, that are useful in the treatment or prevention of diseases or disorders associated with kinases, particularly GSK-3β, c-Abl, HER-1, HER-2, KDR, Flt-3, c-Raf-1, PDGFR-β, c-Kit, Flt-4, Flt-1, Tek, c-src, CDK1, PDK1, FGFR-1, FGFR-2, Fer, MAP3K13, EPHA7 and c-Met kinases. The invention further relates to the use of the compounds of the invention as potent inducers of neurogenesis in embryonic stem cells.

  本发明提供了一种新型的化合物和组合物，其化学式为I：其中R1、R2和R3的定义如本文所述，这些化合物对于治疗或预防与激酶相关的疾病或疾病具有用处，尤其是GSK-3β、c-Abl、HER-1、HER-2、KDR、Flt-3、c-Raf-1、PDGFR-β、c-Kit、Flt-4、Flt-1、Tek、c-src、CDK1、PDK1、FGFR-1、FGFR-2、Fer、MAP3K13、EPHA7和c-Met激酶。本发明进一步涉及将本发明的化合物作为胚胎干细胞神经发生的有效诱导剂使用。
• US7253166B2
  申请人：——

  公开号：US7253166B2

  公开（公告）日：2007-08-07
• [EN] COMPOUNDS THAT INDUCE NEURONAL DIFFERENTIATION IN EMBRYONIC STEM CELLS<br/>[FR] COMPOSES INDUISANT UNE DIFFERENTIATION NEURONALE DANS DES CELLULES SOUCHE EMBRYONNAIRES
  申请人：IRM LLC

  公开号：WO2004093812A2

  公开（公告）日：2004-11-04

  The invention provides a novel class of compounds and compositions that are useful in the treatment or prevention of diseases or disorders associated with kinases, particularly GSK-3ß, c-Abl, HER-1, HER-2, KDR, Flt-3, c-Raf-1, PDGFR- ß, c-Kit, Flt-4, Flt-1, Tek, c-src, CDK1, PDK1, FGFR-1, FGFR-2, Fer, MAP3K13, EPHA7 and c-Met kinases. The invention further relates to the use of the compounds of the invention as potent inducers of neurogenesis in embryonic stem cells.
• Efficient formation of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines: a novel route to TWS119, a glycogen synthase kinase-3β inhibitor
  作者：Anand Mayasundari、Naoaki Fujii

  DOI：10.1016/j.tetlet.2010.05.032

  日期：2010.7

  A concise synthesis of 4,6-disubstituted pyrrolo[2,3-d]pyrimidines is described. The key step involves the formation of an ether or thioether linkage along with concurrent ring closure in one-pot to yield the desired product in only two steps from a common intermediate. The reaction is chemoselective to incorporate phenol, thiophenol, and thiol. This method enabled efficient production of TWS119, a glycogen synthase kinase-3 beta inhibitor. (C) 2010 Elsevier Ltd. All rights reserved.