10-(4-bromobutyl)-1-(phenylsulfonyl)-1,10-dihydropyrrolo[2,3-a]carbazole | 1370364-97-8

• 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-bromobutyl)-1-(phenylsulfonyl)-1,10-dihydropyrrolo[2,3-a]carbazole
• 英文别名: 1-(Benzenesulfonyl)-10-(4-bromobutyl)pyrrolo[2,3-a]carbazole
• CAS: 1370364-97-8
• 化学式: C₂₄H₂₁BrN₂O₂S
• 分子量: 481.413
• InChiKey: BOIKBKRQAHKIEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-(4-bromobutyl)-1-(phenylsulfonyl)-1,10-dihydropyrrolo[2,3-a]carbazole 在 sodium azide 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 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
• 作为产物：
  描述：

  1,4-二溴丁烷 、 1-benzenesulfonyl-1,10-dihydropyrrolo[2,3-a]carbazole 在 sodium hydride 作用下， 以 mineral oil 为溶剂， 反应 4.0h， 以83%的产率得到10-(4-bromobutyl)-1-(phenylsulfonyl)-1,10-dihydropyrrolo[2,3-a]carbazole
  参考文献：
  名称：

  新型吡咯并咔唑-咪唑并苯并咪唑共轭物的合成及生物学活性

  摘要：

  制备了新的吡咯并咔唑-咪唑并苯并咪唑共轭物，并评估了它们对Pim-1激酶的抑制作用，DNA结合和对人肿瘤细胞系的抗增殖活性。结果表明，与衍生化合物相比，吡咯并咔唑Pim抑制剂与咪唑并苯并咪唑衍生物的缀合可以增强缀合物的抗增殖能力。

  DOI：

  10.1016/j.tetlet.2020.152096

文献信息

• Kinase inhibitory potencies and in vitro antiproliferative activities of N-10 substituted pyrrolo[2,3-a]carbazole derivatives
  作者：Rufine Akué-Gédu、Boris Letribot、Emmanuelle Saugues、Eric Debiton、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.bmcl.2012.03.098

  日期：2012.6

  Development of potent and selective Pim kinase inhibitors has recently emerged as an important field for the design of new anti-cancer drugs. We report the synthesis of new N-10-substituted pyrrolo[2,3-a] carbazole derivatives and their evaluation as Pim kinase inhibitors. Moreover, in vitro antiproliferative activity of these compounds was evaluated toward a human fibroblast primary culture and three human solid cancer cell lines (PA1, PC3 and DU145). Compounds 3, 7 and 10 showed inhibitory potencies toward Pim-1 and Pim-3 in the nanomolar range. Additionally, dimethylamino analog 10 also demonstrated interesting sub-micromolar antiproliferative activities toward the cell lines tested. (C) 2012 Elsevier Ltd. All rights reserved.