(Z)-3-(3-bromo-4-hydroxybenzoyl)-5-(3-bromo-4-hydroxybenzylidene)-4-(4-hydroxyphenyl)furan-2(5H)-one

• 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-(3-bromo-4-hydroxybenzoyl)-5-(3-bromo-4-hydroxybenzylidene)-4-(4-hydroxyphenyl)furan-2(5H)-one
• 英文别名: (5Z)-3-(3-bromo-4-hydroxybenzoyl)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-4-(4-hydroxyphenyl)furan-2-one
• 化学式: C₂₄H₁₄Br₂O₆
• 分子量: 558.18
• InChiKey: XEEFBZWDCQZVIL-JMIUGGIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲酸 在 正丁基锂 、 草酰氯 、 硫酸 、 乙酸酐 、 三乙胺 、 二异丙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 (Z)-3-(3-bromo-4-hydroxybenzoyl)-5-(3-bromo-4-hydroxybenzylidene)-4-(4-hydroxyphenyl)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis and antibacterial activities of cadiolides A, B and C and analogues

  摘要：

  The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.010

文献信息

• Synthesis and antibacterial activities of cadiolides A, B and C and analogues
  作者：Agathe Boulangé、Javier Parraga、Abraham Galán、Nuria Cabedo、Stéphane Leleu、Maria Jesus Sanz、Diego Cortes、Xavier Franck

  DOI：10.1016/j.bmc.2015.04.010

  日期：2015.7

  The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils. (C) 2015 Elsevier Ltd. All rights reserved.