(Z)-N-(4-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)phenyl)-3-phenylpropanamide | 1380593-16-7

• 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)-N-(4-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)phenyl)-3-phenylpropanamide
• 英文别名: N-[4-[(5Z)-5-[(4-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]phenyl]-3-phenylpropanamide
• CAS: 1380593-16-7
• 化学式: C₂₆H₂₂N₂O₃S
• 分子量: 442.538
• InChiKey: UDFDMIGIVRAPJE-QJOMJCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-cyanophenyl)-3-phenylpropanamide 、 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26%的产率得到(Z)-N-(4-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)phenyl)-3-phenylpropanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors

  摘要：

  A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold was synthesized as a new series of molecular modifications and extensions of a previously reported series. Compounds were tested in a cell-based and a cell-free assay and furthermore evaluated for their influence on cell viability. The presented substituted thiazolinone scaffold turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. With (Z)-5-(4-methoxybenzylidene)-2-(naphthalen-2-yl)-5H-thiazol-4-one (2k, ST1237), a potent, direct, non-cytotoxic 5-LO inhibitor with IC50 of 0.08 mu M and 0.12 mu M (cell-free assay and intact cells), we present a promising lead optimization and development for further investigations as novel anti-inflammatory drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.003

文献信息

• Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors
  作者：Sebastian Barzen、Carmen B. Rödl、Andreas Lill、Dieter Steinhilber、Holger Stark、Bettina Hofmann

  DOI：10.1016/j.bmc.2012.04.003

  日期：2012.6

  A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold was synthesized as a new series of molecular modifications and extensions of a previously reported series. Compounds were tested in a cell-based and a cell-free assay and furthermore evaluated for their influence on cell viability. The presented substituted thiazolinone scaffold turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. With (Z)-5-(4-methoxybenzylidene)-2-(naphthalen-2-yl)-5H-thiazol-4-one (2k, ST1237), a potent, direct, non-cytotoxic 5-LO inhibitor with IC50 of 0.08 mu M and 0.12 mu M (cell-free assay and intact cells), we present a promising lead optimization and development for further investigations as novel anti-inflammatory drug. (C) 2012 Elsevier Ltd. All rights reserved.