1-pentyl-5-nitro-1H-indole

• 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: 1-pentyl-5-nitro-1H-indole
• 英文别名: 5-Nitro-1-pentylindole
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: IBKNBGCSDDFMEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-pentyl-5-nitro-1H-indole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-pentyl-5-amino-1H-indole
  参考文献：
  名称：

  3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines

  摘要：

  A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-jlquinolin-9-ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G(2)/M phase at 0.1 and 1 mu M and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.

  DOI：

  10.1021/jm070534b
• 作为产物：
  描述：

  1-氯戊烷 、 5-硝基吲哚 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 1-pentyl-5-nitro-1H-indole
  参考文献：
  名称：

  3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines

  摘要：

  A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-jlquinolin-9-ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G(2)/M phase at 0.1 and 1 mu M and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.

  DOI：

  10.1021/jm070534b

文献信息

• <i>N</i>-Heteroaryl Carbamates from Carbon Dioxide <i>via</i> Chemoselective Superbase Catalysis: Substrate Scope and Mechanistic Investigation
  作者：Jere K. Mannisto、Ljiljana Pavlovic、Johannes Heikkinen、Tony Tiainen、Aleksi Sahari、Norbert M. Maier、Kari Rissanen、Martin Nieger、Kathrin H. Hopmann、Timo Repo

  DOI：10.1021/acscatal.3c02362

  日期：2023.9.1

  exposed to CO2, carbamate salts are formed. These can be categorized into two subgroups, stable and fluxional carbamate salts, where the latter undergo fast and reversible CO2 exchange, thus being poor substrates for alkylation. Experiments and DFT calculations indicate that the fluxional behavior is primarily caused by substrate-specific electronic destabilization effects. The degree of destabilization depends

  我们报道了N-杂芳基的温和超碱催化和氮选择性羧化，随后的烷基化能够以良好的产率合成类似药物的O-烷基氨基甲酸酯（平均 86%）。我们的研究结果表明对当前机理的理解进行了部分修改，因为超强碱与吲哚和唑混合后通常会形成不带电的氢键络合物，而不是像之前提出的那样形成离子盐。然而，当这些络合物暴露于CO 2时，形成氨基甲酸盐。这些可以分为两个亚组：稳定的氨基甲酸盐和流动的氨基甲酸盐，其中后者经历快速且可逆的 CO 2交换，因此是烷基化的不良底物。实验和 DFT 计算表明，通量行为主要是由基板特定的电子不稳定效应引起的。不稳定程度取决于杂环结构中氮原子的数量和官能团取代。可以通过使用较低的温度和/或较高的CO 2压力来补偿流动性，因为这两种措施都能充分稳定氨基甲酸盐，从而能够进行后续的烷基化。
• 3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines
  作者：Venusia Gasparotto、Ignazio Castagliuolo、Maria Grazia Ferlin

  DOI：10.1021/jm070534b

  日期：2007.11.1

  A novel series of 3-alkyl-substituted 7-phenyl-3H-pyrrolo[3,2-jlquinolin-9-ones (7-PPyQs) was synthesized with the aim to optimize the cytotoxic activity of recently identified PPyQs, promising inhibitors of tubulin polymerization. All compounds inhibited the growth of 11 human tumor cell lines at submicromolar concentrations as well as two human resistant cancer sublines, A549-T12 and A549-T24. FACS analysis indicated that all compounds caused significant arrest of the A549 cell cycle in G(2)/M phase at 0.1 and 1 mu M and a good correlation between the cytotoxicity IC50 and their ability to block the cell cycle was observed.