1-(5-Fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one | 93513-88-3

• 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-(5-Fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• CAS: 93513-88-3
• 化学式: C₁₅H₁₀F₂O₂
• 分子量: 260.24
• InChiKey: MICVLUDXQZRAIN-UHFFFAOYSA-N

物化性质

• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-Fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one 在 1,4-环己二烯 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.25h， 生成 1-[2-[3-(Diethylamino)-2-hydroxypropoxy]-5-fluorophenyl]-3-(4-fluorophenyl)propan-1-one;hydrochloride
  参考文献：
  名称：

  Optimization of Propafenone Analogues as Antimalarial Leads

  摘要：

  Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile of the drug. A small array of propafenone analogues was designed and synthesized to address the cardiac ion channel and PK liabilities. Testing of this array revealed potent inhibitors of the 3D7 (drug sensitive) and K1 (drug resistant) strains of P. falciparum that possessed significantly reduced ion channel effects and improved metabolic stability. Propafenone analogues are unusual among antimalarial leads in that they are more potent against the multidrug resistant K1 strain of P. falciparum compared to the 3D7 strain.

  DOI：

  10.1021/jm2005546
• 作为产物：
  描述：

  5-氟-2-羟基苯乙酮 、 对氟苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以4.3 g的产率得到1-(5-Fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  氮杂环类化合物及其应用

  摘要：

  本申请属于药物技术领域，具体涉及一种氮杂环类化合物及其应用。本发明公开了一种式(Ⅰ)所示的氮杂环类化合物，或其互变异构体、内消旋体、外消旋体、对映异构体、非对映异构体、药学上可接受的盐、前药、活性代谢物及代谢物的药学上可接受的盐及其混合物形式。经过抗病毒活性实验测定，表明该类化合物具有良好的NS3丝氨酸蛋白酶抑制活性，具有开发成为一种新型的NS3丝氨酸蛋白酶抑制剂的潜力，应用于预防和/或治疗因病毒感染引起的相关疾病。

  公开号：

  CN106632278A

文献信息

• Optimization of Propafenone Analogues as Antimalarial Leads
  作者：David J. Lowes、W. Armand Guiguemde、Michele C. Connelly、Fangyi Zhu、Martina S. Sigal、Julie A. Clark、Andrew S. Lemoff、Joseph L. Derisi、Emily B. Wilson、R. Kiplin Guy

  DOI：10.1021/jm2005546

  日期：2011.11.10

  Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile of the drug. A small array of propafenone analogues was designed and synthesized to address the cardiac ion channel and PK liabilities. Testing of this array revealed potent inhibitors of the 3D7 (drug sensitive) and K1 (drug resistant) strains of P. falciparum that possessed significantly reduced ion channel effects and improved metabolic stability. Propafenone analogues are unusual among antimalarial leads in that they are more potent against the multidrug resistant K1 strain of P. falciparum compared to the 3D7 strain.
• 氮杂环类化合物及其应用
  申请人：黄子为

  公开号：CN106632278A

  公开（公告）日：2017-05-10

  本申请属于药物技术领域，具体涉及一种氮杂环类化合物及其应用。本发明公开了一种式(Ⅰ)所示的氮杂环类化合物，或其互变异构体、内消旋体、外消旋体、对映异构体、非对映异构体、药学上可接受的盐、前药、活性代谢物及代谢物的药学上可接受的盐及其混合物形式。经过抗病毒活性实验测定，表明该类化合物具有良好的NS3丝氨酸蛋白酶抑制活性，具有开发成为一种新型的NS3丝氨酸蛋白酶抑制剂的潜力，应用于预防和/或治疗因病毒感染引起的相关疾病。