(Z)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one | 1272520-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one
• 英文别名: (5Z)-2-(3-fluorophenyl)-5-[(4-methoxyphenyl)methylidene]-1,3-thiazol-4-one
• CAS: 1272520-06-5
• 化学式: C₁₇H₁₂FNO₂S
• 分子量: 313.352
• InChiKey: HJPRUBRUVXSWSI-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氟苯腈 、 4-甲氧基苯甲醛 、 巯基乙酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以40%的产率得到(Z)-2-(3-fluorophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one
  参考文献：
  名称：

  A Class of 5-Benzylidene-2-phenylthiazolinones with High Potency as Direct 5-Lipoxygenase Inhibitors

  摘要：

  A novel class of potent direct 5-lipoxygenase (5-LO) inhibitors bearing a thiazolinone-scaffold identified by virtual screening is presented. A range of substitutions and the importance of the 2-phenyl moiety were evaluated. This series is characterized by high potency in intact polymorphonuclear leukocytes and a cell-free system, exemplified by (Z)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one (18, IC(50) = 0.28 and 0.09 mu M). These disubstituted thiazolinones may possess potential for intervention with inflammatory and allergic diseases and certain cancer types.

  DOI：

  10.1021/jm101165z

文献信息

• A Class of 5-Benzylidene-2-phenylthiazolinones with High Potency as Direct 5-Lipoxygenase Inhibitors
  作者：Bettina Hofmann、Sebastian Barzen、Carmen B. Rödl、Andreas Kiehl、Julia Borig、Aleksandra Živković、Holger Stark、Gisbert Schneider、Dieter Steinhilber

  DOI：10.1021/jm101165z

  日期：2011.3.24

  A novel class of potent direct 5-lipoxygenase (5-LO) inhibitors bearing a thiazolinone-scaffold identified by virtual screening is presented. A range of substitutions and the importance of the 2-phenyl moiety were evaluated. This series is characterized by high potency in intact polymorphonuclear leukocytes and a cell-free system, exemplified by (Z)-2-(4-chlorophenyl)-5-(4-methoxybenzylidene)-5H-thiazol-4-one (18, IC(50) = 0.28 and 0.09 mu M). These disubstituted thiazolinones may possess potential for intervention with inflammatory and allergic diseases and certain cancer types.