N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide | 1454645-90-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide
• CAS: 1454645-90-9
• 化学式: C₁₂H₁₀Br₂N₂O
• 分子量: 358.032
• InChiKey: DNBUGQLVSVUSHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 氢溴酸 、 三乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: oroidin analogues

  摘要：

  The reaction of pyrrole or dibromopyrrole-2-trichloroacetone with various amines results in the series of novel pyrrole-2-carboxamide bearing aromatic heterocycle or aryl or alkyl groups. Synthesized molecules were evaluated for their in vitro antibacterial activities. Most of the compounds exhibited potent activity against both Gram-positive and negative pathogens.

  DOI：

  10.1007/s00044-013-0743-9

文献信息

• Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria
  作者：William T. Barker、Courtney E. Chandler、Roberta J. Melander、Robert K. Ernst、Christian Melander

  DOI：10.1016/j.bmc.2019.03.019

  日期：2019.5

  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.
• Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin
  作者：Lauren Dyson、Anthony D. Wright、Kelly A. Young、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.bmc.2014.01.021

  日期：2014.3

  Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl) allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI(50)) of 42 mu M in MCF-7 (breast) cells and 24 mu M in A2780 (ovarian) cells and >50 mu M in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI(50) values of <5 mu M were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. (C) 2014 Elsevier Ltd. All rights reserved.