10-(4-azidobutyl)-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde | 1370365-01-7

• 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: 10-(4-azidobutyl)-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde
• 英文别名: 10-(4-azidobutyl)-1H-pyrrolo[2,3-a]carbazole-3-carbaldehyde
• CAS: 1370365-01-7
• 化学式: C₁₉H₁₇N₅O
• 分子量: 331.377
• InChiKey: HGQQNLINMKPHMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(4-azidobutyl)-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde 、 2-丙炔-1-醇 在 C₃₃H₃₀Cl₃CuN₄ 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以92%的产率得到10-{4-[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]butyl}-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde
  参考文献：
  名称：

  Use of copper(I) catalyzed azide alkyne cycloaddition (CuAAC) for the preparation of conjugated pyrrolo[2,3-a]carbazole Pim kinase inhibitors

  摘要：

  We have previously demonstrated that pyrrolo[2,3-a]carbazole-3-carbaldehydes are potent Pim kinase inhibitors with in vitro antiproliferative activities. In the present study, we report the synthesis of new pyrrolocarbazoles substituted at the N-10 position. When their ability to inhibit Pim kinase activities were evaluated in in vitro assays, we observed that this nitrogen atom can be substituted without loss of Pim-1 and Pim-3 inhibitory potencies. Moreover, when we added a fluorescent dansyl group (compound 13), we were able to show that 13 penetrates the plasma membrane and enters the cytoplasm. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.009
• 作为产物：
  描述：

  1-benzenesulfonyl-1,10-dihydropyrrolo[2,3-a]carbazole 在 sodium azide 、 sodium hydride 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.0h， 生成 10-(4-azidobutyl)-1,10-dihydropyrrolo[2,3-a]carbazole-3-carbaldehyde
  参考文献：
  名称：

  Use of copper(I) catalyzed azide alkyne cycloaddition (CuAAC) for the preparation of conjugated pyrrolo[2,3-a]carbazole Pim kinase inhibitors

  摘要：

  We have previously demonstrated that pyrrolo[2,3-a]carbazole-3-carbaldehydes are potent Pim kinase inhibitors with in vitro antiproliferative activities. In the present study, we report the synthesis of new pyrrolocarbazoles substituted at the N-10 position. When their ability to inhibit Pim kinase activities were evaluated in in vitro assays, we observed that this nitrogen atom can be substituted without loss of Pim-1 and Pim-3 inhibitory potencies. Moreover, when we added a fluorescent dansyl group (compound 13), we were able to show that 13 penetrates the plasma membrane and enters the cytoplasm. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.009

文献信息

• Use of copper(I) catalyzed azide alkyne cycloaddition (CuAAC) for the preparation of conjugated pyrrolo[2,3-a]carbazole Pim kinase inhibitors
  作者：Boris Letribot、Rufine Akué-Gédu、Niina M. Santio、Malika El-Ghozzi、Daniel Avignant、Federico Cisnetti、Päivi J. Koskinen、Arnaud Gautier、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.ejmech.2012.02.009

  日期：2012.4

  We have previously demonstrated that pyrrolo[2,3-a]carbazole-3-carbaldehydes are potent Pim kinase inhibitors with in vitro antiproliferative activities. In the present study, we report the synthesis of new pyrrolocarbazoles substituted at the N-10 position. When their ability to inhibit Pim kinase activities were evaluated in in vitro assays, we observed that this nitrogen atom can be substituted without loss of Pim-1 and Pim-3 inhibitory potencies. Moreover, when we added a fluorescent dansyl group (compound 13), we were able to show that 13 penetrates the plasma membrane and enters the cytoplasm. (C) 2012 Elsevier Masson SAS. All rights reserved.