3-hexyl-5-(dibromomethylene)-2(5H)-furanone | 199744-23-5

• 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: 3-hexyl-5-(dibromomethylene)-2(5H)-furanone
• 英文别名: 5-(dibromomethylene)-3-hexyl-2(5H)-furanone；3-hexyl-5-dibromomethylene-2(5H)-furanone；5-(dibromomethylidene)-3-hexylfuran-2-one
• CAS: 199744-23-5
• 化学式: C₁₁H₁₄Br₂O₂
• 分子量: 338.039
• InChiKey: MONJZMWYAVRPJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：

  3-hexyl-5-(dibromomethylene)-2(5H)-furanone 在 氨 作用下， 以 二氯甲烷 为溶剂， 生成 5-dibromomethylene-3-hexyl-1,5-dihydropyrrol-2-one
  参考文献：
  名称：

  炔烃取代二氢吡咯酮作为铜绿假单胞菌菌群感应抑制剂的合成

  摘要：

  铜绿假单胞菌的群体感应系统负责致病性和毒力因子的产生和生物膜的形成。先前发现二氢吡咯酮可作为 QS 依赖性细菌表型的抑制剂。在这项研究中，通过内酯中间体的内酯-内酰胺转化合成了一系列二氢吡咯酮 (DHP) 类似物，然后通过 Sonogashira 偶联反应以中等至高产率从溴化二氢吡咯酮形成二氢吡咯酮的新型乙炔类似物。在生物测试中，最有效的化合物 39-40 和 44 在 62.5 µM 时对铜绿假单胞菌报告菌株表现出更高的细菌群体感应抑制 (QSI) 活性。构效关系研究表明，DHPs 环外位置的二炔基取代基比单炔基 DHPs 具有更高的 QSI 活性。此外，DHPs C3 上的己基取代基有利于 QSI 活性，而 DHPs C4 上的苯基取代基不利于类似物的 QSI 活性。

  DOI：

  10.3390/antibiotics11020151
• 作为产物：
  描述：

  Ethyl-β-carethoxy-α-hexyl-levulinat 在 sodium hydroxide 、 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 水 、 甲苯 为溶剂， 反应 9.33h， 生成 3-hexyl-5-(dibromomethylene)-2(5H)-furanone
  参考文献：
  名称：

  硫酸催化的溴化2-烷基乙酰丙酸环化成3-烷基-5-亚甲基-2（5 H）-呋喃酮的再研究

  摘要：

  描述了由烷基取代的乙酰丙酸衍生物通过溴化和酸促进的内酯化合成乙基，丁基，己基和十二烷基取代的溴化物。使用乙酰丙酸作为模型，研究了潜在的反应，并讨论了改变溴化条件和改变酸浓度对产物分布的影响。二溴化在CHCl 3中进行得最好，在无EtOH的CHCl 3中进行，而不会形成酯。在98–100％H 2 SO 4中伴随氧化发生环化反应，但在100％H 2 SO 4中产生环戊内酯的产率最高。还描述了相关的贝克雷利物质的形成。

  DOI：

  10.1016/s0040-4020(97)10034-5

文献信息

• Design, Synthesis, and Evaluation of Fimbrolide–Nitric Oxide Donor Hybrids as Antimicrobial Agents
  作者：Samuel K. Kutty、Nicolas Barraud、Amy Pham、George Iskander、Scott A. Rice、David StC. Black、Naresh Kumar

  DOI：10.1021/jm400951f

  日期：2013.12.12

  in bacteria controlling biofilm formation and virulence factor. Nitric oxide (NO) at sublethal concentration has also been reported to induce dispersal of bacterial biofilms and increase their susceptibility toward standard biocides and antibiotics. Therefore, the combination of QS inhibitors and NO donors has the potential to control the development of biofilm and promote their dispersion via a nonbactericidal

  来自海藻的溴环己内酯显示出对群体感应（QS）的有希望的活性，群体感应是细菌控制生物膜形成和毒力因子的主要调控和交流系统。还报道了亚致死浓度的一氧化氮（NO）会引起细菌生物膜的扩散并增加其对标准杀生物剂和抗生素的敏感性。因此，QS抑制剂和NO供体的组合具有控制生物膜发展并通过非杀菌机制促进其分散的潜力。受这些想法的启发，设计并合成了新的fimbrolide-NO供体杂化化合物。Fimbrolide-NO杂种6b，6f和14a生物发光铜绿假单胞菌QS报告基因检测法和生物膜抑制检测法显示，与非杂合天然溴环十二烷相比，抗菌素被发现作为抗菌剂特别有效。值得注意的是，这些氟溴化物-NO杂化物代表了基于细菌QS抑制和NO信号传导的第一种双重作用抗菌剂。
• [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。
• Production of furanones
  申请人：Biosignal Australia Pty Limited

  公开号：EP1787988A2

  公开（公告）日：2007-05-23

  The present invention relates to the side chain functionalisation of fimbrolides (halogenated 3-alkyl-5-methylene-2(5H)-furanones) and their synthetic analogues, that yields fimbrolides substituted with a halogen, an oxygen or a nitrogen functionality in the alkyl chain, especially fimbrolide alcohols, carboxylate and sulfinate and sulfonate esters, ethers, aldehydes, ketones, acids, amides, nitro derivatives, hydrophobic, hydrophilic and fluorophilic alkyl derivatives and polymers.

  本发明涉及芬普罗内酯（卤代 3-烷基-5-亚甲基-2(5H)-呋喃酮）及其合成类似物的侧链官能化，从而得到在烷基链中被卤素、氧或氮官能团取代的芬普罗内酯，特别是芬普罗内酯醇、羧酸酯、硫酸酯和磺酸酯、醚、醛、酮、酸、酰胺、硝基衍生物、疏水性、亲水性和亲氟烷基衍生物及聚合物。
• 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.