(Z)-2-Cyano-3-hydroxy-4-(4-trifluoromethyl-phenyl)-but-2-enoic acid (4-trifluoromethyl-phenyl)-amide | 136186-48-6

• 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)-2-Cyano-3-hydroxy-4-(4-trifluoromethyl-phenyl)-but-2-enoic acid (4-trifluoromethyl-phenyl)-amide
• 英文别名: (Z)-2-cyano-3-hydroxy-N,4-bis[4-(trifluoromethyl)phenyl]but-2-enamide
• CAS: 136186-48-6
• 化学式: C₁₉H₁₂F₆N₂O₂
• 分子量: 414.307
• InChiKey: XVSWCKHTRYEEHJ-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  对三氟甲基苯胺 在 sodium hydride 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.33h， 生成 (Z)-2-Cyano-3-hydroxy-4-(4-trifluoromethyl-phenyl)-but-2-enoic acid (4-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Synthesis and biological activity of a series of diaryl-substituted .alpha.-cyano-.beta.-hydroxypropenamides, a new class of anthelmintic agents

  摘要：

  A series of alpha-cyano-beta-hydroxypropenamides was prepared and tested for anthelmintic activity. Alpha-cyano-beta-hydroxy hydroxy-N-[4-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]propenamide (1) showed good activity against the nematode Nematospirodes dubius in a mixed parasite infection in mice; several of the analogues were also effective against the cestode Hymenolepis nana. In sheep trials, 1 caused 100% reduction of the hematophagous nematode Haemonchus contortus after a single dose of 20 mg/kg but did not show satisfactory control of Trichostrongylus colubriformis or Ostertagia circumcincta. Against the liver fluke Fasciola hepatica, 1 suppressed egg production but only temporarily, suggesting that the adult flukes were not eliminated. Mechanism of action studies on 1 using Ascaris mitochondria showed it to be an uncoupler of oxidative phosphorylation.

  DOI：

  10.1021/jm00115a020

文献信息

• Synthesis and biological activity of a series of diaryl-substituted .alpha.-cyano-.beta.-hydroxypropenamides, a new class of anthelmintic agents
  作者：Eric B. Sjogren、Michael A. Rider、Peter H. Nelson、Stanford Bingham、Anthony L. Poulton、Mark A. Emanuel、Richard Komuniecki

  DOI：10.1021/jm00115a020

  日期：1991.11

  A series of alpha-cyano-beta-hydroxypropenamides was prepared and tested for anthelmintic activity. Alpha-cyano-beta-hydroxy hydroxy-N-[4-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]propenamide (1) showed good activity against the nematode Nematospirodes dubius in a mixed parasite infection in mice; several of the analogues were also effective against the cestode Hymenolepis nana. In sheep trials, 1 caused 100% reduction of the hematophagous nematode Haemonchus contortus after a single dose of 20 mg/kg but did not show satisfactory control of Trichostrongylus colubriformis or Ostertagia circumcincta. Against the liver fluke Fasciola hepatica, 1 suppressed egg production but only temporarily, suggesting that the adult flukes were not eliminated. Mechanism of action studies on 1 using Ascaris mitochondria showed it to be an uncoupler of oxidative phosphorylation.