2,2,2-Trichloro-1-[4,5-dibromo-1-(2-phenylethyl)pyrrol-2-yl]ethanone | 1060676-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trichloro-1-[4,5-dibromo-1-(2-phenylethyl)pyrrol-2-yl]ethanone
• CAS: 1060676-99-4
• 化学式: C₁₄H₁₀Br₂Cl₃NO
• 分子量: 474.406
• InChiKey: VLTVSZWYJHMQCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-1-[4,5-dibromo-1-(2-phenylethyl)pyrrol-2-yl]ethanone 、 4-(3-aminopropyl)-1H-imidazol-2-ylamine dihydrochloride 在 4-二甲氨基吡啶 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-[3-(2-amino-1H-imidazol-5-yl)propyl]-4,5-dibromo-1-(2-phenylethyl)pyrrole-2-carboxamide
  参考文献：
  名称：

  Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii

  摘要：

  Bacteria of the genus Acinetobacter spp. are rapidly emerging as problematic pathogens in healthcare settings. This is exacerbated by the bacteria's ability to form robust biofilms. Marine natural products incorporating a 2-aminoimidazole (2-AI) motif, namely from the oroidin class of marine alkaloids, have served as a unique scaffold for developing molecules that have the ability to inhibit and disperse bacterial biofilms. Herein we present the anti-biofilm activity of a small library of second generation oroidin analogues against the bacterium Acinetobacter baumannii. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.089
• 作为产物：
  描述：

  Ethanone, 2,2,2-trichloro-1-(1-ethyl-1H-pyrrol-2-yl)- 在 溴 作用下， 以 氯仿 为溶剂， 以57%的产率得到2,2,2-Trichloro-1-[4,5-dibromo-1-(2-phenylethyl)pyrrol-2-yl]ethanone
  参考文献：
  名称：

  Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii

  摘要：

  Bacteria of the genus Acinetobacter spp. are rapidly emerging as problematic pathogens in healthcare settings. This is exacerbated by the bacteria's ability to form robust biofilms. Marine natural products incorporating a 2-aminoimidazole (2-AI) motif, namely from the oroidin class of marine alkaloids, have served as a unique scaffold for developing molecules that have the ability to inhibit and disperse bacterial biofilms. Herein we present the anti-biofilm activity of a small library of second generation oroidin analogues against the bacterium Acinetobacter baumannii. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.089

文献信息

• Antibiofilm Activity of a Diverse Oroidin Library Generated through Reductive Acylation
  作者：T. Eric Ballard、Justin J. Richards、Arianexys Aquino、Catherine S. Reed、Christian Melander

  DOI：10.1021/jo802260t

  日期：2009.2.20

  A diverse 20-compound library of analogues based on the marine alkaloid oroidin were synthesized via a reductive acylation strategy. The final target was then assayed for inhibition and dispersion activity against common proteo-bacteria known to form biofilms. This methodology represents a significant improvement over the generality of known methods to acylate substrates containing 2-aminoimidazoles and has the potential to have broad application to the synthesis of more advanced oroidin family members and their corresponding analogues.
• Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii
  作者：Justin J. Richards、Catherine S. Reed、Christian Melander

  DOI：10.1016/j.bmcl.2008.06.089

  日期：2008.8

  Bacteria of the genus Acinetobacter spp. are rapidly emerging as problematic pathogens in healthcare settings. This is exacerbated by the bacteria's ability to form robust biofilms. Marine natural products incorporating a 2-aminoimidazole (2-AI) motif, namely from the oroidin class of marine alkaloids, have served as a unique scaffold for developing molecules that have the ability to inhibit and disperse bacterial biofilms. Herein we present the anti-biofilm activity of a small library of second generation oroidin analogues against the bacterium Acinetobacter baumannii. (c) 2008 Elsevier Ltd. All rights reserved.