ethyl 8-methyl-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate | 1334218-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 8-methyl-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate
• CAS: 1334218-37-9
• 化学式: C₁₈H₂₀N₄O₅
• 分子量: 372.381
• InChiKey: YGQPSAICCHEDOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112.28
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 8-methyl-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以70%的产率得到ethyl 5-amino-8-methyl-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate
  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 、 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 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 ethyl 8-methyl-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1,6-dihydropyrrolo[2,3-g]indazole-7-carboxylate
  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