4,5-dibromopyrrole-2-carboxamide | 34649-20-2

• 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: 4,5-dibromopyrrole-2-carboxamide
• 英文别名: 4,5-dibromopyrrole-2-carbamide；4,5-dibromopyrrole-2-carbonamide；4,5-Dibromo-1h-pyrrole-2-carboxamide
• CAS: 34649-20-2
• 化学式: C₅H₄Br₂N₂O
• 分子量: 267.908
• InChiKey: VTWHNVAKXBNGFV-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±42.0 °C(Predicted)
• 密度：
  2.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-dibromopyrrole-2-carboxamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到4,5-dibromo-1H-pyrrole-2-carbothioamide
  参考文献：
  名称：

  噻唑基卤代吡咯或吡唑作为新型抗菌剂和抗生物膜剂的设计、合成和生物学评价

  摘要：

  生物膜的形成是细菌产生耐药性的重要因素之一。设计并合成了一系列含有噻唑基团的卤代吡咯或吡唑作为抗菌剂，以针对生物膜。其中，化合物对多种革兰氏阳性菌均表现出抗菌活性，特别是对万古霉素耐药菌（MIC≤0.125 μg/mL）。此外，该化合物在亚 MIC 剂量下可显着抑制生物膜形成。此外，与吡咯霉素 C 相比，该化合物表现出显着较低的哺乳动物细胞毒性，并且还评估了其在不同物种中的肝微粒体代谢稳定性。进一步的感染模型实验证明该化合物是有效的。

  DOI：

  10.1016/j.ejmech.2024.116221
• 作为产物：
  描述：

  2,2,2-三氯-1-(4,5-二溴-1H-吡咯-2-基)-1-乙酮 在 ammonium hydroxide 作用下， 反应 0.75h， 以78%的产率得到4,5-dibromopyrrole-2-carboxamide
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1005591826613

文献信息

• Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles
  作者：Diana Wischang、Madlen Radlow、Jens Hartung

  DOI：10.1039/c3dt51582f

  日期：——

  aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon–bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with

  来自褐藻Ascophyllum nodosum的溴过氧化物酶，缩写为V Br PO（An I）和V Br PO（An II），显示出41％的序列同源性，并且α-螺旋二级结构的百分比相差两倍。蛋白质单体组成V Br PO（An I）的同二聚体和V Br PO（An II）的六聚体。溴过氧化物酶II与过氧化氢和溴化物的结合强度比V Br PO（An一世）。在氧化催化中，溴过氧化物酶I和II类似地快速转移过氧化氢和溴化物，生成吗啉-4-乙磺酸（MES）缓冲的叔丁醇水溶液（pH 6.2）分子溴作为亲电烃溴化试剂。诸如三溴化物和次溴酸之类的替代化合物尚不具有足够的亲电子性，无法直接参与碳-溴键的形成。从溴到次溴酸从溴到三溴化物的亲电性下降在前沿分子轨道（FMO）分析中与烯烃的π型HOMO和σ* Br，X之间的较大能隙相关型LUMO的溴化试剂。通过这种方法，可以预测底物的反应性和在钒酸盐依赖性溴过氧化
• Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations
  作者：Diana Wischang、Jens Hartung

  DOI：10.1016/j.tet.2011.04.010

  日期：2011.6

  Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 degrees C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 mu mol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4-ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2-carboxamide (from Acanthella carteri). (C) 2011 Elsevier Ltd. All rights reserved.