4-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine | 1334217-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 4-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine
• 英文别名: indazole
• CAS: 1334217-99-0
• 化学式: C₁₂H₁₃IN₄O₃
• 分子量: 388.165
• InChiKey: DQNZWYSQRZEQBL-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  541.1±50.0 °C(Predicted)
• 密度：
  2.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  96.21
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine 在 copper(l) iodide 、 四(三苯基膦)钯 、 铜 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 二丁醚 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3,6-dihydropyrazolo[3,4-c]carbazole
  参考文献：
  名称：

  Identification of 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles as new Pim kinase inhibitors

  摘要：

  New 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles were prepared and evaluated for their Pim kinase inhibitory potencies as well as their antiproliferative activities toward two prostatic cancer cell lines. Pyrazolocarbazole 15a was found to be a potent Pim kinase modulator with inhibitory potency toward the three isoforms. Compound 6c strongly inhibited Pim-3 with weaker effect toward Pim-1 and Pim-2, and thus could be used as an interesting molecular tool to study Pim-3 biological functions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.011
• 作为产物：
  描述：

  6-硝基吲唑 在 1,4-环己二烯 、 硫酸 、 palladium 10% on activated carbon 、 potassium nitrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine
  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 pyrazolo[4,3-a]phenanthridines, a new scaffold for Pim kinase inhibition
  作者：Virginie Suchaud、Laurent Gavara、Francis Giraud、Lionel Nauton、Vincent Théry、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.bmc.2014.07.011

  日期：2014.9

  A new series of nitro or amino substituted pyrazolo[4,3-a]phenanthridines was synthesized in 6 steps from 5-bromo-6-nitroindazole. The evaluation of their inhibitory potency toward Pim kinases demonstrated that the nitro series could be considered as an interesting starting point for the development of new Pim kinase inhibitors, especially Pim-3. A preferential binding mode was suggested by molecular modeling experiments for nitro series and Pim-1/Pim-3 ATP-binding sites. Moreover, the most active compounds exhibited antiproliferative activities toward PC3 cells in the micromolar range.