1-(1-benzyl-4,5-dibromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one | 1060676-94-9

• 分子结构分类: 有机化合物
• 英文名称: 1-(1-benzyl-4,5-dibromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one
• 英文别名: trichloro-1-(4,5-dibromo-1-butyl-1H-pyrrol-2-yl)ethan-1-one
• CAS: 1060676-94-9
• 化学式: C₁₃H₈Br₂Cl₃NO
• 分子量: 460.38
• InChiKey: NBBSLKQFAKUCIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  色胺 、 1-(1-benzyl-4,5-dibromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以53%的产率得到N-(2-(1H-indol-3-yl)ethyl)-1-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

  摘要：

  The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

  DOI：

  10.1016/j.bmc.2019.03.019
• 作为产物：
  描述：

  N-benzyl-2-trichloroacetylpyrrole 在 溴 作用下， 以 氯仿 为溶剂， 生成 1-(1-benzyl-4,5-dibromo-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one
  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