(Z)-3-bromo-4-(2-methoxyphenyl)-5-(4-(trifluoromethyl)-benzylidene)furan-2(5H)-one | 1402571-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-bromo-4-(2-methoxyphenyl)-5-(4-(trifluoromethyl)-benzylidene)furan-2(5H)-one
• 英文别名: (Z)-3-bromo-4-(2-methoxyphenyl)-5-[4-(trifluoromethyl)benzylidene]furan-2(5H)-one；(Z)-3-bromo-4-(2-methoxyphenyl)-5-(4-trifluoromethylbenzylidene)furan-2(5H)-one；(5Z)-3-bromo-4-(2-methoxyphenyl)-5-[[4-(trifluoromethyl)phenyl]methylidene]furan-2-one
• CAS: 1402571-39-4
• 化学式: C₁₉H₁₂BrF₃O₃
• 分子量: 425.202
• InChiKey: MKLKSTKLGXONIS-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-3-bromo-4-(2-methoxyphenyl)-5-(4-(trifluoromethyl)-benzylidene)furan-2(5H)-one 、 异丁胺 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到3-bromo-5-[4-(trifluoromethyl)benzyl]-5-hydroxy-1-isobutyl-4-(2-methoxyphenyl)pyrrol-2(5H)-one
  参考文献：
  名称：

  Inhibition of Enterococcus faecalis biofilm formation by highly active lactones and lactams analogues of rubrolides

  摘要：

  Seven beta-aryl substituted gamma-alkylidene-gamma-lactones analogues of rubrolides were synthesized from mucobromic acid and converted through a lactamization with isobutylamine into their corresponding gamma-hydroxy-gamma-lactams (76-85%). These lactams were converted into (Z)- and (E)-gamma-alkylidene-gamma-lactams (23 -45%). All compounds were fully characterized by IR, NMR (H-1 and C-13), COSY and HETCOR bidimensional experiments, and NOE difference spectroscopy experiments when necessary. Evaluation of these three different classes of compounds against Enterococcus faecalis biofilm formation showed that all classes are active and the highest biofilm inhibition activity was caused by lactam 13f (IC50 = 0.76 mu g/mL). Moreover, in almost all cases at least one of the lactams is more active than its correspondent gamma-alkylidene-gamma-lactone. The use of rubrolides as a lead structure has proven successful for the identification of new compounds displaying novel antibacterial activities, namely biofilm inhibition, which have the potential for the development of antimicrobial drugs targeted to inhibition of the initial stages of bacterial infections, rather than bacterial viability. Such drugs are less prompt to induce bacterial resistance, being therefore a more cost-effective investment for pharmaceutical research. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.035
• 作为产物：
  描述：

  3-bromo-4-(2-methoxyphenyl)furan-2(5H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-3-bromo-4-(2-methoxyphenyl)-5-(4-(trifluoromethyl)-benzylidene)furan-2(5H)-one
  参考文献：
  名称：

  Inhibition of Enterococcus faecalis biofilm formation by highly active lactones and lactams analogues of rubrolides

  摘要：

  Seven beta-aryl substituted gamma-alkylidene-gamma-lactones analogues of rubrolides were synthesized from mucobromic acid and converted through a lactamization with isobutylamine into their corresponding gamma-hydroxy-gamma-lactams (76-85%). These lactams were converted into (Z)- and (E)-gamma-alkylidene-gamma-lactams (23 -45%). All compounds were fully characterized by IR, NMR (H-1 and C-13), COSY and HETCOR bidimensional experiments, and NOE difference spectroscopy experiments when necessary. Evaluation of these three different classes of compounds against Enterococcus faecalis biofilm formation showed that all classes are active and the highest biofilm inhibition activity was caused by lactam 13f (IC50 = 0.76 mu g/mL). Moreover, in almost all cases at least one of the lactams is more active than its correspondent gamma-alkylidene-gamma-lactone. The use of rubrolides as a lead structure has proven successful for the identification of new compounds displaying novel antibacterial activities, namely biofilm inhibition, which have the potential for the development of antimicrobial drugs targeted to inhibition of the initial stages of bacterial infections, rather than bacterial viability. Such drugs are less prompt to induce bacterial resistance, being therefore a more cost-effective investment for pharmaceutical research. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.035

文献信息

• Synthesis of Rubrolide Analogues as New Inhibitors of the Photosynthetic Electron Transport Chain
  作者：Luiz C. A. Barbosa、Célia R. A. Maltha、Mateus R. Lage、Rosimeire C. Barcelos、Alice Donà、José W. M. Carneiro、Giuseppe Forlani

  DOI：10.1021/jf302921n

  日期：2012.10.24

  used as a model for the development of new drugs and agrochemicals. Following this strategy 11 rubrolide analogues, bearing electron-withdrawing and -donating groups at both benzene rings, were prepared starting from commercially available mucobromic acid. The ability of all compounds to inhibit the photosynthetic electron transport chain in the chloroplast was investigated. The rubrolide analogues

  许多天然产物已被用作开发新药和农用化学品的模型。按照这种策略，从市售的粘溴酸开始制备11个在两个苯环上带有吸电子和给电子基团的rubrolide类似物。研究了所有化合物抑制叶绿体中光合作用电子传输链的能力。rubrolide类似物有效地干扰了光驱动的铁氰化物被分离的叶绿体还原。IC 50实际上，活性最高的衍生物的值仅比具有相同作用方式的商业除草剂（例如Diuron（0.27μM））高1个数量级。QSAR研究表明，最有效的化合物是通过还原过程或亲电反应机理具有更高电子接受能力的化合物。所获得的结果表明，卢布内酯类似物代表了开发靶向光合作用的新活性成分用作除草剂的有前途的候选者。