4-(1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamine | 1174038-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 4-(1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamine
• 英文别名: 4-(1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine
• CAS: 1174038-48-2
• 化学式: C₁₁H₉N₅
• 分子量: 211.226
• InChiKey: ULPADEPZZAIIOV-UHFFFAOYSA-N

物化性质

• 沸点：
  596.6±60.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 24.33h， 生成 4-(1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-ylamine
  参考文献：
  名称：

  Developing DYRK inhibitors derived from the meridianins as a means of increasing levels of NFAT in the nucleus

  摘要：

  A structure-activity relationship has been developed around the meridianin scaffold for inhibition of Dyrk1a. The compounds have been focussed on the inhibition of kinase Dyrk1a, as a means to retain the transcription factor NFAT in the nucleus. NFAT is responsible for up-regulation of genes responsible for the induction of a slow, oxidative skeletal muscle phenotype, which may be an effective treatment for diseases where exercise capacity is compromised. The SAR showed that while strong Dyrk1a binding was possible with the meridianin scaffold the compounds have no effect on NFAT localisation, however, by moving from the indole to a 6-azaindole scaffold both potent Dyrk1a binding and increased NFAT residence time in the nucleus were obtained - properties not observed with the reported Dyrk1a inhibitors. One compound was shown to be effective in an ex vivo muscle fiber assay. The increased biological activity is thought to arise from the added interaction between the azaindole nitrogen and the lysine residue in the back pocket. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.037

文献信息

• 4 (PYRROLO[2,3-C]PYRIDINE-3-YL)PYRIMIDIN-2-AMINE DERIVATIVES
  申请人：Dorsch Dieter

  公开号：US20100292262A1

  公开（公告）日：2010-11-18

  Compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 and R 5 have the meanings indicated in Claim 1 , are inhibitors of cell proliferation/cell vitality and can be employed for the treatment of tumours.

  式（I）化合物中，其中R1、R2、R3、R4和R5的含义如权利要求书中所示，是细胞增殖/细胞活力的抑制剂，可用于肿瘤的治疗。
• 4-(PYRROLOÝ2,3-C¨PYRIDINE-3-YL)-PYRIMIDIN-2-AMIN-DERIVATIVE
  申请人：Merck Patent GmbH

  公开号：EP2231664A1

  公开（公告）日：2010-09-29
• SUBSTITUTED PYRIMIDINE BMI-1 INHIBITORS
  申请人：PTC Therapeutics, Inc.

  公开号：EP3039015B1

  公开（公告）日：2019-10-30
• [DE] 4-(PYRROLO[2,3-C]PYRIDINE-3-YL)-PYRIMIDIN-2-AMIN-DERIVATIVE<br/>[EN] 4-(PYRROLO[2,3-C]PYRIDINE-3-YL)-PYRIMIDINE-2-AMINE DERIVATIVES<br/>[FR] DÉRIVÉS DE 4-(PYRROLO[2,3-C]PYRIDINE-3-YL)-PYRIMIDINE-2-AMINE
  申请人：MERCK PATENT GMBH

  公开号：WO2009092431A1

  公开（公告）日：2009-07-30

  Verbindungen der Formel (I) worin R1, R2, R3, R4 und R5 die in Anspruch 1 angegebenen Bedeutungen haben, sind lnhibitoren der Zellproliferation/Zellvitalitat und können zur Behandlung von Tumoren eingesetzt werden.
• Developing DYRK inhibitors derived from the meridianins as a means of increasing levels of NFAT in the nucleus
  作者：Simon J. Shaw、Dane A. Goff、Nan Lin、Rajinder Singh、Wei Li、John McLaughlin、Kristen A. Baltgalvis、Donald G. Payan、Todd M. Kinsella

  DOI：10.1016/j.bmcl.2017.03.037

  日期：2017.6

  A structure-activity relationship has been developed around the meridianin scaffold for inhibition of Dyrk1a. The compounds have been focussed on the inhibition of kinase Dyrk1a, as a means to retain the transcription factor NFAT in the nucleus. NFAT is responsible for up-regulation of genes responsible for the induction of a slow, oxidative skeletal muscle phenotype, which may be an effective treatment for diseases where exercise capacity is compromised. The SAR showed that while strong Dyrk1a binding was possible with the meridianin scaffold the compounds have no effect on NFAT localisation, however, by moving from the indole to a 6-azaindole scaffold both potent Dyrk1a binding and increased NFAT residence time in the nucleus were obtained - properties not observed with the reported Dyrk1a inhibitors. One compound was shown to be effective in an ex vivo muscle fiber assay. The increased biological activity is thought to arise from the added interaction between the azaindole nitrogen and the lysine residue in the back pocket. (C) 2017 Elsevier Ltd. All rights reserved.