4-[(E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoyl]benzoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[(E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoyl]benzoic acid
• 化学式: C₁₈H₁₀F₆O₃
• 分子量: 388.266
• InChiKey: YEWXUNHAFDRRSP-LZCJLJQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 、 4-乙酰基苯甲酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以16%的产率得到4-[(E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoyl]benzoic acid
  参考文献：
  名称：

  Antibacterial chalcones––bioisosteric replacement of the 4′-hydroxy group

  摘要：

  Hydroxy chalcones, for example, Licochalcone A, has for several years been known to be antibacterial. The low aqueous solubility and the medium antibacterial potency have limited the usefulness of the compounds. We describe the bioisosteric replacement of the essential 4'-hydroxy group in the hydroxy chalcones with bioisosters of varied degrees of acidity resulting in both more potent and more soluble compounds. The more acidic 4'-hydroxy analogues (e.g., 3'-fluoro- or 3',5'-difluoro-) gave almost inactive compounds whereas exchanging the hydroxy group with a carboxy group resulted in a potent compound with a high aqueous solubility. Further optimisation and SAR-analysis resulted in soluble and potent carboxy chalcones [e.g., 3,5-dibromo- and 3,5-di(trifluoromethyl)-]. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.071

文献信息

• Antibacterial chalcones––bioisosteric replacement of the 4′-hydroxy group
  作者：Simon Feldbæk Nielsen、Thomas Boesen、Mogens Larsen、Kristian Schønning、Hasse Kromann

  DOI：10.1016/j.bmc.2004.03.071

  日期：2004.6

  Hydroxy chalcones, for example, Licochalcone A, has for several years been known to be antibacterial. The low aqueous solubility and the medium antibacterial potency have limited the usefulness of the compounds. We describe the bioisosteric replacement of the essential 4'-hydroxy group in the hydroxy chalcones with bioisosters of varied degrees of acidity resulting in both more potent and more soluble compounds. The more acidic 4'-hydroxy analogues (e.g., 3'-fluoro- or 3',5'-difluoro-) gave almost inactive compounds whereas exchanging the hydroxy group with a carboxy group resulted in a potent compound with a high aqueous solubility. Further optimisation and SAR-analysis resulted in soluble and potent carboxy chalcones [e.g., 3,5-dibromo- and 3,5-di(trifluoromethyl)-]. (C) 2004 Elsevier Ltd. All rights reserved.