4,5-dibromo-1H-pyrrole-2-carboxylic acid (2-hydroxyethyl) amide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,5-dibromo-1H-pyrrole-2-carboxylic acid (2-hydroxyethyl) amide
• 英文别名: 4,5-dibromo-N-(2-hydroxyethyl)-1H-pyrrole-2-carboxamide；4,5-dibromo-N-(2-hydroxyethyl)-1h-pyrrole-2-carboxamide
• 化学式: C₇H₈Br₂N₂O₂
• 分子量: 311.961
• InChiKey: NWWDLIZVQNSCMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基肉桂酰氯 、 4,5-dibromo-1H-pyrrole-2-carboxylic acid (2-hydroxyethyl) amide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-2-(4,5-dibromo-1H-pyrrole-2-carboxamido)ethyl 3-(3,4-dimethoxyphenyl)acrylate
  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
• 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 6.0h， 生成 4,5-dibromo-1H-pyrrole-2-carboxylic acid (2-hydroxyethyl) amide
  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

• ——
  作者：Thomas Lindel、Holger Hoffmann、Matthias Hochgürtel、Joseph R. Pawlik

  DOI：10.1023/a:1005591826613

  日期：——

  We investigated the relationship between the structures of pyrrole-containing alkaloids from marine sponges of the genus Agelas and their capacity to deter feeding by the omnivorous Caribbean reef fish, Thalassoma bifasciatum. Seven natural products were assayed at volumetric concentrations of 1, 5, and 10 mg/ml: dispacamide A, keramadine, oroidin, midpacamide, 4,5-dibromopyrrole-2-carboxylic acid, 4,5-dibromopyrrole-2-carboxamide, and racemic longamide A. We also assayed 14 structural analogs obtained mostly by chemical synthesis. Of the seven natural products, only rac-longamide A was not significantly deterrent at any of the assay concentrations. The pyrrole moiety was required for feeding inhibition activity, while the addition of the imidazole group enhanced this activity. Variously functionalized imidazoles lacking the pyrrole moiety were not deterrent. Combinations of the natural products appeared to have an additive effect on feeding inhibition; there was no evidence of synergy. Given their high concentrations in sponge tissue, dispacamide A and oroidin most probably serve as the primary chemical defenses of many Agelas sp., while minor compounds such as keramadine are not present in high enough concentrations to contribute much to chemical defense.
• Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: oroidin analogues
  作者：Balaram S. Takale、Neha V. Desai、Afsar Ali Siddiki、Hemchandra K. Chaudhari、Vikas N. Telvekar

  DOI：10.1007/s00044-013-0743-9

  日期：2014.3

  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.