1-(5-Fluoro-2-hydroxyphenyl)-3-phenylpropan-1-one | 1341230-18-9

• 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-phenylpropan-1-one
• CAS: 1341230-18-9
• 化学式: C₁₅H₁₃FO₂
• 分子量: 244.265
• InChiKey: SLCUMIFQVRDMGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-Fluoro-2-hydroxyphenyl)-3-phenylpropan-1-one 在 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-phenylpropan-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：

  苯甲醛 在 1,4-环己二烯 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(5-Fluoro-2-hydroxyphenyl)-3-phenylpropan-1-one
  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