1-(5-bromo-1-ethyl-1H-indol-3-yl)ethan-1-one

• 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-(5-bromo-1-ethyl-1H-indol-3-yl)ethan-1-one
• 英文别名: 1-(5-bromo-1-ethylindol-3-yl)ethanone
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.137
• InChiKey: LRYXTKNJICMEES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 1-(5-bromo-1-ethyl-1H-indol-3-yl)ethan-1-one 、 N,N-二甲基乙酰胺 反应 1.0h， 生成
  参考文献：
  名称：

  Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria

  摘要：

  In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.

  DOI：

  10.1021/acsmedchemlett.8b00161
• 作为产物：
  描述：

  3-(5-溴-1H-吲哚-3-基)-3-氧代丙酰胺 在 四丁基溴化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.52h， 生成 1-(5-bromo-1-ethyl-1H-indol-3-yl)ethan-1-one
  参考文献：
  名称：

  Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst

  摘要：

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。

  DOI：

  10.2174/157017811799304395

文献信息

• Towards the syntheses of<i>N</i>-H and<i>N</i>-alkylated derivatives of meridianins
  作者：Bernard Corbel、FrançOis Michaud、Laurent Meijer、Gaëlle Simon、Hélène Couthon-Gourves、Jean-Pierre Haelters、Nelly Kervarec

  DOI：10.1002/jhet.5570440407

  日期：2007.7

  Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved

  通过使用DMF-DMA将N-甲苯磺酰基-3-乙酰基吲哚或N-烷基-3-乙酰基吲哚经两步转化为相应的烯胺酮，合成了经络胺的新型N- H和N-烷基化衍生物作为潜在的抗肿瘤药。或不添加吡咯烷。用胍进一步环化得到相应的2-氨基嘧啶。由此获得的化合物的结构通过1 H和13 C NMR光谱，NOE实验和X射线分析证明。
• Novel and Simple Methodology for the Synthesis of 3-Acetylindoles and their N-Alkyl Derivatives Using TBAB as Phase Transfer Catalyst
  作者：M. Venkatanarayana、Pramod K. Dubey

  DOI：10.2174/157017811799304395

  日期：2011.11.1

  Using 5% aq. NaOH, a simple method for the transformation of 3-cyanoacetylindoles 2(a-e) into 3- acetylindoles 3 (a-e), in good yields, is reported. Tetrabutylammoniumbromide (TBAB) is found to be an efficient phase transfer catalyst for the synthesis of N-alkyl derivatives 5(a-t) of 3-acetylindoles 3(a-e) giving products in excellent yields. 2 (a-e) were themselves obtained from simple indoles 1 (a-e) by reaction with cyano acetic acid in the presence of propionic anhydride at 100 °C for 5-10 min. Partial hydrolysis of 2 (a-e) under hot acidic conditions yielded the corresponding carboxamides α-(3-indolecarboxoyl)acetamides 4(a-e). Which could be readily transformed into the respective 3(a-e) by refluxing with 5% aq. NaOH for 2-2.5 h.

  报道了一种利用5%氢氧化钠水溶液，将3-氰基乙酰基吲哚2(a-e)高效转化为3-乙酰基吲哚3(a-e)的简便方法。四丁基溴化铵（TBAB）被发现是一种有效的相转移催化剂，用于合成3-乙酰基吲哚3(a-e)的N-烷基衍生物5(a-t)，产率优异。2(a-e)本身是通过吲哚1(a-e)与氰基乙酸在丙酸酐存在下于100°C反应5-10分钟得到的。在热酸性条件下部分水解2(a-e)，得到相应的羧酰胺α-(3-吲哚羧酰基)乙酰胺4(a-e)，这些羧酰胺可以通过与5%氢氧化钠水溶液回流2-2.5小时，容易地转化为相应的3(a-e)。
• Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria
  作者：William M. Huggins、William T. Barker、James T. Baker、Nicholas A. Hahn、Roberta J. Melander、Christian Melander

  DOI：10.1021/acsmedchemlett.8b00161

  日期：2018.7.12

  In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.