1-n-butyl-5-nitro-1H-indole | 857893-05-1

• 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-n-butyl-5-nitro-1H-indole
• 英文别名: 1-butyl-5-nitro-1H-indole；1-n-butyl-5-nitroindole；SGT1631；N-(n-butyl)-5-nitroindole；1-Butyl-5-nitroindole
• CAS: 857893-05-1
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: SOQYDPSOOPHQAB-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °C
• 沸点：
  368.9±15.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-n-butyl-5-nitro-1H-indole 在 三乙基硅烷 、 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 SGT₁₆₅₇
  参考文献：
  名称：

  Selective Inhibition of the Periodontal Pathogen Porphyromonas gingivalis by Third-Generation Zafirlukast Derivatives

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c01471
• 作为产物：
  描述：

  1-碘丁烷 、 5-硝基吲哚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以38 %的产率得到1-n-butyl-5-nitro-1H-indole
  参考文献：
  名称：

  THIOL ISOMERASES INHIBITORS; PREPARATION THEREOF; AND METHODS OF USE THEREOF

  摘要：

  Disclosed are novel thiol isomerase inhibitors and their use in the prevention or treatment of the development or progression of a disease or condition involving one or more of the extracellular thiol isomerases. Further disclosed a method for preventing or treating thrombosis, a thrombotic disease, platelet aggregation, fibrin generation, an infectious disease, a viral disease, an immune disorder, inflammation, a neurologic disease, a neurodegenerative disorder, a cancer or a combination thereof in a patient, comprising: administering to the patient in need thereof a therapeutically effective amount of a compound.

  公开号：

  WO2024039822A1

文献信息

• Syntheses of Novel Indole Lipoic Acid Derivatives and Their Antioxidant Effects on Lipid Peroxidation
  作者：A. Selen Gurkan、Arzu Karabay、Zeliha Buyukbingol、Adeboye Adejare、Erdem Buyukbingol

  DOI：10.1002/ardp.200400932

  日期：2005.3

  properties of conjugates based on indole and lipoic acid moieties. The design and syntheses of novel indole α‐lipoic acid derivatives were performed. The antioxidant properties of target compounds were investigated using rat liver microsomal, NADPH‐dependent lipid peroxidation inhibition. Some of the target compounds, especially those containing amide linker at position 5 of indole ring, proved to be highly

  该研究的目的是检查基于吲哚和硫辛酸部分的缀合物的抗氧化特性。进行了新型吲哚α-硫辛酸衍生物的设计和合成。使用大鼠肝微粒体、NADPH 依赖性脂质过氧化抑制研究了目标化合物的抗氧化特性。与α-硫辛酸相比，一些目标化合物，特别是那些在吲哚环的第5位含有酰胺接头的化合物，被证明在抑制脂质过氧化方面非常有效。
• [EN] MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS<br/>[FR] MODULATEURS DES TRANSPORTEURS DE LA CASSETTE DE LIAISON À L'ATP
  申请人：VERTEX PHARMA

  公开号：WO2010054138A2

  公开（公告）日：2010-05-14

  Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator ("CFTR"). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明的化合物及其药学上可接受的组成物，可作为ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子（“CFTR”）。本发明还涉及使用本发明的化合物治疗ABC转运蛋白介导的疾病的方法。
• Cu(II)-Catalyzed H/D exchange of indole derivatives
  作者：Jing-Wen Bai、Lei Guo、Meng-Zhe Chen、Rigoberto Advincula、Hong-Hai Zhang

  DOI：10.1016/j.tetlet.2023.154884

  日期：2024.1

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• 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.
• Nitro-substituted 3,3′-bis(indolyl)methane derivatives as anion receptors: Electron-withdrawing effect and tunability of anion binding properties
  作者：Litao Wang、Wei Wei、Yong Guo、Jian Xu、Shijun Shao

  DOI：10.1016/j.saa.2010.12.004

  日期：2011.2

  A series of nitro-substituted 3,3'-bis-indolyl phenylmethane derivatives were synthesized and their anion binding properties were investigated in detail. The introduction of the electron-withdrawing nitro group into indole unit and/or meso-phenyl ring, which leads to the increased acidity of indole NH and meso-position CH proton, has a positive effect on anion binding. The nitro-substituted bis(indolyl)methane receptors exhibited selective colorimetric sensing of F- anion, as revealed by the notable color and spectral changes, rationally due to the deprotonation of the indole NH of the receptor. Meanwhile, the additive introduction of the nitro substituents on the meso-phenyl ring of bis(indolyl)methane can lead to the deprotonation of the meso-position CH and further induce an irreversible oxidation process obtaining bis(indolyl)methene product in the F- anion sensing system. (C) 2010 Elsevier B.V. All rights reserved.