5-nitro-8-phenyl-1,6-dihydropyrrolo[2,3-g]indazole | 1334218-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-nitro-8-phenyl-1,6-dihydropyrrolo[2,3-g]indazole
• CAS: 1334218-39-1
• 化学式: C₁₅H₁₀N₄O₂
• 分子量: 278.27
• InChiKey: IMXNSLXJEYDPGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.61
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-nitro-8-phenyl-1,6-dihydropyrrolo[2,3-g]indazole 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以78%的产率得到
  参考文献：
  名称：

  Identification of pyrrolo[2,3-g]indazoles as new Pim kinase inhibitors

  摘要：

  The synthesis and Pim kinase inhibition potency of a new series of pyrrolo[2,3-g] indazole derivatives is described. The results obtained in this preliminary structure-activity relationship study pointed out that sub-micromolar Pim-1 and Pim-3 inhibitory potencies could be obtained in this series, more particularly for compounds 10 and 20, showing that pyrrolo[2,3-g] indazole scaffold could be used for the development of new potent Pim kinase inhibitors. Molecular modeling experiments were also performed to study the binding mode of these compounds in Pim-3 ATP-binding pocket. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.074
• 作为产物：
  描述：

  6-硝基吲唑 在 四(三苯基膦)钯 、 1,4-环己二烯 、 硫酸 、 palladium 10% on activated carbon 、 potassium carbonate 、 对甲苯磺酸 、 potassium nitrate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 5-nitro-8-phenyl-1,6-dihydropyrrolo[2,3-g]indazole
  参考文献：
  名称：

  Synthesis of 1,6-dihydropyrrolo[2,3-g]indazoles using Larock indole annulation

  摘要：

  The synthesis of 1,6-dihydropyrrolo[2,3-g]indazole derivatives is described. The indolic ring system is constructed via a Larock palladium-catalyzed annulation using terminal and internal alkynes. Additionally, when using internal alkynes for this reaction, we found that a directing effect on regioselectivity was mediated by the ester group of alkyl 3-substituted propiolate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.029

文献信息

• Synthesis of 1,6-dihydropyrrolo[2,3-g]indazoles using Larock indole annulation
  作者：Laurent Gavara、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.tet.2011.07.029

  日期：2011.9

  The synthesis of 1,6-dihydropyrrolo[2,3-g]indazole derivatives is described. The indolic ring system is constructed via a Larock palladium-catalyzed annulation using terminal and internal alkynes. Additionally, when using internal alkynes for this reaction, we found that a directing effect on regioselectivity was mediated by the ester group of alkyl 3-substituted propiolate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Identification of pyrrolo[2,3-g]indazoles as new Pim kinase inhibitors
  作者：Laurent Gavara、Virginie Suchaud、Lionel Nauton、Vincent Théry、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.bmcl.2013.02.074

  日期：2013.4

  The synthesis and Pim kinase inhibition potency of a new series of pyrrolo[2,3-g] indazole derivatives is described. The results obtained in this preliminary structure-activity relationship study pointed out that sub-micromolar Pim-1 and Pim-3 inhibitory potencies could be obtained in this series, more particularly for compounds 10 and 20, showing that pyrrolo[2,3-g] indazole scaffold could be used for the development of new potent Pim kinase inhibitors. Molecular modeling experiments were also performed to study the binding mode of these compounds in Pim-3 ATP-binding pocket. (C) 2013 Elsevier Ltd. All rights reserved.