1-butyl-5-(dibromomethylene)-3-hexyl-1H-pyrrol-2-one | 664336-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1-butyl-5-(dibromomethylene)-3-hexyl-1H-pyrrol-2-one
• 英文别名: 1-butyl-5-dibromomethylene-3-hexyl-1,5-dihydropyrrol-2-one；1-Butyl-5-(dibromomethylidene)-3-hexylpyrrol-2-one
• CAS: 664336-20-3
• 化学式: C₁₅H₂₃Br₂NO
• 分子量: 393.162
• InChiKey: HBCGHEKSZAOCRI-UHFFFAOYSA-N

物化性质

• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正丁胺 、 3-hexyl-5-(dibromomethylene)-2(5H)-furanone 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以64%的产率得到1-butyl-5-(dibromomethylene)-3-hexyl-1H-pyrrol-2-one
  参考文献：
  名称：

  Synthesis, quorum sensing inhibition and docking studies of 1,5-dihydropyrrol-2-ones

  摘要：

  Gram-negative bacteria such as Pseudomonas aeruginosa and Escherichia coli use N-acylated L-homoserine lactones (AHLs) as autoinducers (AIs) for quorum sensing (QS), a chief regulatory and cell-to-cell communication system. QS is responsible for social adaptation, virulence factor production, biofilm production and antibiotic resistance in bacteria. Fimbrolides, a class of halogenated furanones isolated from the red marine alga Delisea pulchra, have been shown to exhibit promising QS inhibitory activity against various Gram-negative and Gram-positive bacterial strains. In this work, various lactam analogues of fimbrolides viz., 1,5-dihydropyrrol-2-ones, were designed and synthesized via an efficient lactamization protocol. All the synthesized analogues were tested for QS inhibition against the E. coli AHL-monitor strain JB357 gfp (ASV). Compound 17a emerged as the most potent compound, followed by 9c, with AIC(40) values (the ratio of synthetic inhibitor to natural AHL signaling molecule that is required to lower GFP expression to 40%) of 1.95 and 19.00, respectively. Finally, the potential binding interactions between the synthesized molecules and the LasR QS receptor were studied by molecular docking. Our results indicate that 1,5-dihydropyrrol-2-ones have the ability to serve as potential leads for the further development of novel QS inhibitors as antimicrobial therapeutics. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.10.025

文献信息

• Furanone derivatives and methods of making same
  申请人：Kumar Naresh

  公开号：US20050215772A1

  公开（公告）日：2005-09-29

  Novel synthesis methods, to the products of such novel methods, and to uses of these products. In particular, the present invention provides methods for the reactions of furanones, in particular fimbrolides, with amines. The invention has particular application in the synthesis of halogenated 1,5-dihydro-pyrrol-2-one, 5-halomethylene substituted 1,5-dihydropyrrol-2-ones (lactam analogues of fimbriolides), 5-amino substituted furanones and 5-aminomethylene-2(5H)-furanones and their synthetic analogues. The invention also relates to novel compounds and uses thereof.

  本发明涉及新型合成方法、这些新型方法的产物及其用途。具体而言，本发明提供了一种将呋喃酮，特别是纤毛菌素与胺反应的方法。本发明在合成卤代1,5-二氢吡咯-2-酮、5-卤代亚甲基取代的1,5-二氢吡咯-2-酮（纤毛菌素的内酰胺类似物）、5-氨基取代的呋喃酮和5-氨基亚甲基-2（5H）-呋喃酮及其合成类似物方面具有特殊的应用。本发明还涉及新的化合物及其用途。
• Hydroxamate compositions
  申请人：Covidien LP

  公开号：EP2564859A1

  公开（公告）日：2013-03-06

  The present disclosure provides compositions including a first component including at least one phospholipid possessing at least one vinyl group, a second component including a furanone possessing vinyl and/or acrylate groups, and a third component including a hydroxamate. Compositions, medical devices, and coatings including copolymers and blends of the foregoing components are also provided.

  本公开提供的组合物包括：第一组分（包括至少一种具有至少一个乙烯基的磷脂）、第二组分（包括一种具有乙烯基和/或丙烯酸酯基团的呋喃酮）和第三组分（包括一种羟肟酸酯）。此外，还提供了包括上述组分的共聚物和混合物的组合物、医疗器械和涂料。
• ANTIMICROBIAL MATERIALS AND COATINGS
  申请人：Covidien LP

  公开号：EP2160192B1

  公开（公告）日：2018-03-28
• HYDROXAMATE COMPOSITIONS
  申请人：Stopek Joshua

  公开号：US20100093846A1

  公开（公告）日：2010-04-15

  The present disclosure provides compositions including a first component including at least one phospholipid possessing at least one vinyl group, a second component including a furanone possessing vinyl and/or acrylate groups, and a third component including a hydroxamate. Compositions, medical devices, and coatings including copolymers and blends of the foregoing components are also provided.
• FURANONE COPOLYMERS
  申请人：Stopek Joshua B.

  公开号：US20100130713A1

  公开（公告）日：2010-05-27

  The present disclosure provides copolymers including a first monomer including at least one phospholipid possessing at least one vinyl group and a second monomer including a furanone possessing vinyl and/or acrylate groups. Compositions, medical devices, and coatings including such copolymers are also provided.