1-(2,4-dichlorophenyl)-3-(4-isopropylphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2,4-dichlorophenyl)-3-(4-isopropylphenyl)prop-2-en-1-one
• 英文别名: 1-(2,4-Dichlorophenyl)-3-(4-propan-2-ylphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₆Cl₂O
• 分子量: 319.23
• InChiKey: QNACANRYKGGFLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-3-(4-isopropylphenyl)prop-2-en-1-one 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 乙腈 为溶剂， 反应 17.25h， 生成 1-[(2,4-dichlorophenyl)[4-(4-isopropylphenyl)-1H-pyrrol-3-yl]methyl]-1H-imidazole
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1H-pyrrolyl)(phenyl)methyl-1H-imidazole Derivatives as Antiprotozoal Agents

  摘要：

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.

  DOI：

  10.1021/acs.jmedchem.8b01464
• 作为产物：
  描述：

  4-异丙基苯甲醛 、 2,4-二氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以93%的产率得到1-(2,4-dichlorophenyl)-3-(4-isopropylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1H-pyrrolyl)(phenyl)methyl-1H-imidazole Derivatives as Antiprotozoal Agents

  摘要：

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.

  DOI：

  10.1021/acs.jmedchem.8b01464