(E)-N-(5-cinnamoyl-4-methylthiazol-2-yl)benzamide

• 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: (E)-N-(5-cinnamoyl-4-methylthiazol-2-yl)benzamide
• 英文别名: N-[4-methyl-5-[(E)-3-phenylprop-2-enoyl]-1,3-thiazol-2-yl]benzamide
• 化学式: C₂₀H₁₆N₂O₂S
• 分子量: 348.425
• InChiKey: IWAJRPXIIOADQX-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-苄基-2-硫脲 在 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 (E)-N-(5-cinnamoyl-4-methylthiazol-2-yl)benzamide
  参考文献：
  名称：

  Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase

  摘要：

  A hybrid pharmacophore approach is used to design and synthesize novel chalcone-thiazole hybrid molecules. Herein, thiazole has been hybridized with chalcone to obtain a new class of 5-LOX inhibitors. In vitro biological evaluation showed that most of the compounds were better 5-LOX inhibitors than the positive control, Zileuton (IC50 = 1.05 +/- 0.03 mu M). The best compounds in the series, namely, 4k, 4n, and 4v (4k: IC50 = 0.07 +/- 0.02 mu M, 4n: IC50 = 0.08 +/- 0.05 mu M, 4v: 0.12 +/- 0.04 mu M) are found to be 10 times more active than previously reported 2-amino thiazole (2m: IC50 = 0.9 +/- 0.1 mu M) by us. Further, 4k has redox (noncompetitive) while 4n and 4v act through a competitive inhibition mechanism. SAR indicated that the presence of methoxy/methyl either in the vicinity of chalcone or both thiazole and chalcone contributed to the synergistic inhibitory effect.

  DOI：

  10.1021/acsmedchemlett.9b00193

文献信息

• Chalcone-Thiazole Hybrids: Rational Design, Synthesis, and Lead Identification against 5-Lipoxygenase
  作者：Shweta Sinha、S. L. Manju、Mukesh Doble

  DOI：10.1021/acsmedchemlett.9b00193

  日期：2019.10.10

  A hybrid pharmacophore approach is used to design and synthesize novel chalcone-thiazole hybrid molecules. Herein, thiazole has been hybridized with chalcone to obtain a new class of 5-LOX inhibitors. In vitro biological evaluation showed that most of the compounds were better 5-LOX inhibitors than the positive control, Zileuton (IC50 = 1.05 +/- 0.03 mu M). The best compounds in the series, namely, 4k, 4n, and 4v (4k: IC50 = 0.07 +/- 0.02 mu M, 4n: IC50 = 0.08 +/- 0.05 mu M, 4v: 0.12 +/- 0.04 mu M) are found to be 10 times more active than previously reported 2-amino thiazole (2m: IC50 = 0.9 +/- 0.1 mu M) by us. Further, 4k has redox (noncompetitive) while 4n and 4v act through a competitive inhibition mechanism. SAR indicated that the presence of methoxy/methyl either in the vicinity of chalcone or both thiazole and chalcone contributed to the synergistic inhibitory effect.