(Z)-3-bromo-5-(4-trifluoromethylbenzylidene)-1-isobutyl-4-(2-methoxyphenyl)pyrrol-2(5H)-one | 1561859-33-3

• 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-5-(4-trifluoromethylbenzylidene)-1-isobutyl-4-(2-methoxyphenyl)pyrrol-2(5H)-one
• 英文别名: (5Z)-3-bromo-4-(2-methoxyphenyl)-1-(2-methylpropyl)-5-[[4-(trifluoromethyl)phenyl]methylidene]pyrrol-2-one
• CAS: 1561859-33-3
• 化学式: C₂₃H₂₁BrF₃NO₂
• 分子量: 480.324
• InChiKey: FIPATZKBNNEYFD-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-bromo-4-(2-methoxyphenyl)furan-2(5H)-one 在 对甲苯磺酸 、 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 、 氯仿 为溶剂， 反应 9.0h， 生成 (Z)-3-bromo-5-(4-trifluoromethylbenzylidene)-1-isobutyl-4-(2-methoxyphenyl)pyrrol-2(5H)-one 、 (E)-3-bromo-5-(4-trifluoromethylbenzylidene)-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

文献信息

• Inhibition of Enterococcus faecalis biofilm formation by highly active lactones and lactams analogues of rubrolides
  作者：Ulisses A. Pereira、Luiz C.A. Barbosa、Célia R.A. Maltha、Antônio J. Demuner、Mohammed A. Masood、Andréa L. Pimenta

  DOI：10.1016/j.ejmech.2014.05.035

  日期：2014.7

  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.