N-(3,5-bis(trifluoromethyl)phenyl)-3-(2,3,4-trimethoxyphenyl)acrylamide | 1147840-55-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(3,5-bis(trifluoromethyl)phenyl)-3-(2,3,4-trimethoxyphenyl)acrylamide
• 英文别名: N-[3,5-bis(trifluoromethyl)phenyl]-3-(2,3,4-trimethoxyphenyl)prop-2-enamide
• CAS: 1147840-55-8
• 化学式: C₂₀H₁₇F₆NO₄
• 分子量: 449.35
• InChiKey: GILAFTMRNSJCHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,3,4-三甲氧基肉桂酸 、 间二(三氟甲基)苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以67.6%的产率得到N-(3,5-bis(trifluoromethyl)phenyl)-3-(2,3,4-trimethoxyphenyl)acrylamide
  参考文献：
  名称：

  Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of Helicobacter pylori: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination

  摘要：

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

  DOI：

  10.1021/jm8015602