4-bromo-1-ethyl-1H-indole | 1194375-88-6

• 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: 4-bromo-1-ethyl-1H-indole
• 英文别名: N-ethyl-4-bromoindole；1-ethyl-4-bromoindole；4-bromo-1-ethylindole
• CAS: 1194375-88-6
• 化学式: C₁₀H₁₀BrN
• 分子量: 224.1
• InChiKey: ZAYNZVWIRUKCAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-bromo-1-ethyl-1H-indole 在 正丁基锂 、 palladium 10% on activated carbon 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 3-(1-Ethylindol-4-yl)chromen-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,4,5-Substituted Pyrimidines as a New Class of Tubulin Polymerization Inhibitors

  摘要：

  Members of a series of 2,4,5-substituted pyrimidine derivatives were synthesized, and their interactions with tubulin and their antiproliferative activities against the human hepatocellular carcinoma cells of liver (BEL-7402) were evaluated. One member of this family, the indole-pyrimidine 4k, having an indole-aryl-substituted aminopyrimidine structure, was observed to be an excellent inhibitor of tubulin polymerization (IC50 = 0.79 mu M) and to display significantly high antiproliferative activities against several cancer cell lines with IC50 values ranging from 16 to 62 nM. This substance displayed a high propensity to arrests cells at the G(2)/M phase of the cell cycle (EC50 = 20 nM). In addition, 4k was found to competitively inhibit colchicine binding to tubulin, indicating that it binds to the colchicine-binding site of tubulin. The observations made in this investigation demonstrate that 2,4,5-substituted pyrimidines represent a new class of tubulin polymerization inhibitors with significant antiproliferative activity.

  DOI：

  10.1021/jm101388d
• 作为产物：
  描述：

  4-溴吲哚 、 三氟乙酸乙酯 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.12h， 以64%的产率得到4-bromo-1-ethyl-1H-indole
  参考文献：
  名称：

  一种乙基化反应的微波辅助合成方法

  摘要：

  本发明涉及一种乙基化反应的微波辅助合成方法。其特征在于，包括：反应底物在有机溶剂中，三氟乙酸乙酯作为乙基化试剂，在碱的存在下，微波辅助加热2 min即可得到相应的乙基化产物。本发明开辟一种新的乙基化反应的方法，该方法的反应速率比传统方法快数倍，操作简便，成本低廉，反应时间短，底物适用范围广，还可以避免使用价格昂贵或剧毒性的乙基化试剂，具有较高的应用价值。

  公开号：

  CN110272323A

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF DIHYDROFOLATE REDUCTASE<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE LA DIHYDROFOLATE RÉDUCTASE
  申请人：CIDARA THERAPEUTICS INC

  公开号：WO2016201219A1

  公开（公告）日：2016-12-15

  The disclosure relates to compositions and methods for the treatment of fungal, bacterial, and parasitic infections and inhibition of fungal, bacterial, and parasitic growth. In particular, such compositions include dihydrofolate reductase (DHFR) inhibitors that are able to bind to DHFR and inhibit its function, resulting in inhibition of DNA biosynthesis and reduced cell division. The disclosure features DHFR inhibitors having a diaminoquinazoline scaffold.

  该披露涉及用于治疗真菌、细菌和寄生虫感染以及抑制真菌、细菌和寄生虫生长的组合物和方法。具体来说，这些组合物包括能够结合到二氢叶酸还原酶（DHFR）并抑制其功能的DHFR抑制剂，从而抑制DNA合成和减少细胞分裂。该披露涉及具有二氨基喹唑啉骨架的DHFR抑制剂。
• Controllable synthesis of 3-chloro- and 3,3-dichloro-2-oxindoles <i>via</i> hypervalent iodine-mediated chlorooxidation
  作者：Xinpeng Jiang、Liechao Yang、Wenlong Yang、Yu Zhu、Liyun Fang、Chuanming Yu

  DOI：10.1039/c9ob01173k

  日期：——

  3-dichloro-2-oxindoles has been developed via hypervalent iodine-promoted chlorooxidation. By using two equivalents of 1-chloro-1,2-benziodoxol-3-(1H)-one, a wide range of indoles were transformed into 3-chloro-2-oxindoles in DMF/CF3CO2H/H2O at room temperature with good yields. As far as we know, this is the first report on the selective C-2 oxidation and C-3 monochlorination of simple indoles. In

  通过高价碘促进的氯氧化，已经开发出一种有效且可控制的合成3-氯-和3,3-二氯-2-氧吲哚的方案。通过在室温下使用两当量的1-氯-1,2-苯并恶唑-3-（1H）-一，将各种吲哚在DMF / CF3CO2H / H2O中转化为3-氯-2-氧吲哚。据我们所知，这是有关简单吲哚选择性C-2氧化和C-3单氯化的首次报道。此外，在优化的条件下（二恶烷/ H2O，80°C），三当量的相同高价碘以高达99％的产率提供3,3-二氯-2-氧吲哚。该方法具有温和的反应条件，广泛的底物可用性和良好的官能团耐受性。
• 一种取代吲哚直接合成3-氯羟吲哚类化合物 的方法
  申请人：浙江工业大学

  公开号：CN108047120B

  公开（公告）日：2019-11-12

  本发明涉及一种取代吲哚直接合成3‑氯羟吲哚类化合物的方法，其特征在于向装有有机溶剂和水的反应瓶中加入高碘试剂和吲哚底物，在0~80℃下反应1~300min后加入饱和碳酸氢钠溶液淬灭反应，最后萃取分离、纯化得到产物3‑氯羟吲哚化合物；本发明的主要创新点在于利用廉价的高碘试剂对吲哚直接氧化氯代合成3‑氯羟吲哚，具有合成成本低、操作简便、条件温和、底物普适性好和反应收率较高等优点。
• Synthesis and Biological Evaluation of 2,4,5-Substituted Pyrimidines as a New Class of Tubulin Polymerization Inhibitors
  作者：Fuchun Xie、Hongbing Zhao、Dewen Li、Hong Chen、Haitian Quan、Xiaojing Shi、Liguang Lou、Youhong Hu

  DOI：10.1021/jm101388d

  日期：2011.5.12

  Members of a series of 2,4,5-substituted pyrimidine derivatives were synthesized, and their interactions with tubulin and their antiproliferative activities against the human hepatocellular carcinoma cells of liver (BEL-7402) were evaluated. One member of this family, the indole-pyrimidine 4k, having an indole-aryl-substituted aminopyrimidine structure, was observed to be an excellent inhibitor of tubulin polymerization (IC50 = 0.79 mu M) and to display significantly high antiproliferative activities against several cancer cell lines with IC50 values ranging from 16 to 62 nM. This substance displayed a high propensity to arrests cells at the G(2)/M phase of the cell cycle (EC50 = 20 nM). In addition, 4k was found to competitively inhibit colchicine binding to tubulin, indicating that it binds to the colchicine-binding site of tubulin. The observations made in this investigation demonstrate that 2,4,5-substituted pyrimidines represent a new class of tubulin polymerization inhibitors with significant antiproliferative activity.
• 一种乙基化反应的微波辅助合成方法
  申请人：广东石油化工学院

  公开号：CN110272323A

  公开（公告）日：2019-09-24

  本发明涉及一种乙基化反应的微波辅助合成方法。其特征在于，包括：反应底物在有机溶剂中，三氟乙酸乙酯作为乙基化试剂，在碱的存在下，微波辅助加热2 min即可得到相应的乙基化产物。本发明开辟一种新的乙基化反应的方法，该方法的反应速率比传统方法快数倍，操作简便，成本低廉，反应时间短，底物适用范围广，还可以避免使用价格昂贵或剧毒性的乙基化试剂，具有较高的应用价值。