5-(4-hydroxybenzylidene)-3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)thiazolidin-4-one | 1280722-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-hydroxybenzylidene)-3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)thiazolidin-4-one
• 英文别名: 5-[(4-hydroxyphenyl)methylidene]-3-[(4-methoxyphenyl)methyl]-2-[(4-methoxyphenyl)methylimino]-1,3-thiazolidin-4-one
• CAS: 1280722-96-4
• 化学式: C₂₆H₂₄N₂O₄S
• 分子量: 460.554
• InChiKey: ZZWKLNFLUWJIHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  71.36
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxybenzylidene)-3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)thiazolidin-4-one 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 丙酮 、 甲醇 、 水 为溶剂， 反应 18.0h， 以70%的产率得到2-(4-((3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)-4-oxothiazolidin-5-ylidene)methyl) phenoxy)acetic acid
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014
• 作为产物：
  描述：

  4-甲氧基苄胺 在 哌啶 、 三乙醇胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 5-(4-hydroxybenzylidene)-3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)thiazolidin-4-one
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014