3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile | 1240613-84-6

• 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: 3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile
• CAS: 1240613-84-6
• 化学式: C₁₈H₁₈ClNO₃
• 分子量: 331.799
• InChiKey: FMDKCPJMYWXGEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以80%的产率得到3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzoic acid
  参考文献：
  名称：

  Identification and Development of Novel Inhibitors of Toxoplasma gondii Enoyl Reductase

  摘要：

  Toxoplasmosis causes significant morbidity and mortality, and yet available medicines are limited by toxicities and hypersensitivity. Because improved medicines are needed urgently, rational approaches were used to identify novel lead compounds effective against Toxoplasma gondii enoyl reductase (TgENR), a type II fatty acid synthase enzyme essential in parasites but not present in animals. Fifty-three compounds, including three classes that inhibit ENRs, were tested. Six compounds have antiparasite MIC(90)s <= 6 mu M without toxicity to host cells, three compounds have IC(90)s < 45 nM against recombinant TgENR, and two protect mice. To further understand the mode of inhibition, the cocrystal structure of one of the most promising candidate compounds in complex with TgENR has been determined to 2.7 angstrom. The crystal structure reveals that the aliphatic side chain of compound 19 occupies, as predicted, space made available by replacement of a bulky hydrophobic residue in homologous bacterial ENRs by Ala in TgENR. This provides a paradigm, conceptual foundation, reagents, and lead compounds for future rational development and discovery of improved inhibitors of T. gondii.

  DOI：

  10.1021/jm9017724
• 作为产物：
  描述：

  4-丙基-2,6-二甲氧基苯酚 、 3-氯-4-氟苯腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以93%的产率得到3-chloro-4-(2,6-dimethoxy-4-propylphenoxy)benzonitrile
  参考文献：
  名称：

  Identification and Development of Novel Inhibitors of Toxoplasma gondii Enoyl Reductase

  摘要：

  Toxoplasmosis causes significant morbidity and mortality, and yet available medicines are limited by toxicities and hypersensitivity. Because improved medicines are needed urgently, rational approaches were used to identify novel lead compounds effective against Toxoplasma gondii enoyl reductase (TgENR), a type II fatty acid synthase enzyme essential in parasites but not present in animals. Fifty-three compounds, including three classes that inhibit ENRs, were tested. Six compounds have antiparasite MIC(90)s <= 6 mu M without toxicity to host cells, three compounds have IC(90)s < 45 nM against recombinant TgENR, and two protect mice. To further understand the mode of inhibition, the cocrystal structure of one of the most promising candidate compounds in complex with TgENR has been determined to 2.7 angstrom. The crystal structure reveals that the aliphatic side chain of compound 19 occupies, as predicted, space made available by replacement of a bulky hydrophobic residue in homologous bacterial ENRs by Ala in TgENR. This provides a paradigm, conceptual foundation, reagents, and lead compounds for future rational development and discovery of improved inhibitors of T. gondii.

  DOI：

  10.1021/jm9017724