4-bromo-3-hexyl-5-bromomethylene-2(5H)-furanone | 664336-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-bromo-3-hexyl-5-bromomethylene-2(5H)-furanone
• 英文别名: 4-bromo-5-(bromomethylidene)-3-hexylfuran-2-one
• CAS: 664336-09-8
• 化学式: C₁₁H₁₄Br₂O₂
• 分子量: 338.039
• InChiKey: FLVMUOPUHKLSSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-3-hexyl-5-bromomethylene-2(5H)-furanone 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 (5Z)-4-bromo-5-(bromomethylidene)-1-butyl-3-hexylpyrrol-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

• [EN] FURANONE DERIVATIVES AND METHODS OF MAKING SAME<br/>[FR] DERIVES DE FURANONE ET LEURS PROCEDES DE PRODUCTION
  申请人：BIOSIGNAL PTY LTD

  公开号：WO2004016588A1

  公开（公告）日：2004-02-26

  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 fimbrolides), 5-amino substituted furanones and 5-aminomethylene-2(5H)-furanones and their synthetic analogues. The invention also relates to novel compounds and uses thereof.

  本发明涉及新颖的合成方法，新方法的产物以及这些产物的用途。特别地，本发明提供了一种将呋喃酮（尤其是fimbrolides）与胺反应的方法。本发明在卤代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（fimbrolides的内酰胺类似物），5-氨基取代呋喃酮和5-氨基亚甲基-2（5H）-呋喃酮及其合成类似物的合成中具有特定应用。本发明还涉及新化合物及其用途。
• 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。
• Synthesis, quorum sensing inhibition and docking studies of 1,5-dihydropyrrol-2-ones
  作者：Wai-Kean Goh、Christopher R. Gardner、Kondapalli V.G. Chandra Sekhar、Nripendra N. Biswas、Shashidhar Nizalapur、Scott A. Rice、Mark Willcox、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2015.10.025

  日期：2015.12

  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.