N-<3-chloro-4-(4'-chlorophenoxy)phenyl>cyanoacetamide | 136186-50-0

• 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: N-<3-chloro-4-(4'-chlorophenoxy)phenyl>cyanoacetamide
• 英文别名: N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-cyanoacetamide
• CAS: 136186-50-0
• 化学式: C₁₅H₁₀Cl₂N₂O₂
• 分子量: 321.163
• InChiKey: VFRKBPKNKDLCCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.12
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-三氟甲基苯甲酰氯 、 N-<3-chloro-4-(4'-chlorophenoxy)phenyl>cyanoacetamide 在 sodium hydride 作用下， 生成 (Z)-N-[3-Chloro-4-(4-chloro-phenoxy)-phenyl]-2-cyano-3-hydroxy-3-(4-trifluoromethyl-phenyl)-acrylamide
  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
• 作为产物：
  描述：

  3,4-二氯硝基苯 在 盐酸 、 sodium hydride 、 tin(ll) chloride 、 N,N'-二异丙基碳二亚胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 N-<3-chloro-4-(4'-chlorophenoxy)phenyl>cyanoacetamide
  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