3-(4-Fluorophenyl)-1-[2-(oxiran-2-ylmethoxy)phenyl]propan-1-one | 1341230-21-4

• 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: 3-(4-Fluorophenyl)-1-[2-(oxiran-2-ylmethoxy)phenyl]propan-1-one
• CAS: 1341230-21-4
• 化学式: C₁₈H₁₇FO₃
• 分子量: 300.33
• InChiKey: YRUBZOZJPYEJMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Fluorophenyl)-1-[2-(oxiran-2-ylmethoxy)phenyl]propan-1-one 在 palladium 10% on activated carbon 作用下， 以 乙醇 、 环己烯 为溶剂， 反应 0.42h， 生成 1-[2-[3-[4-(4-Aminophenyl)piperazin-1-yl]-2-hydroxypropoxy]phenyl]-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：

  3-(4-氟苯基)-1-(2-羟基苯基)丙-2-烯-1-酮 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 18.0h， 生成 3-(4-Fluorophenyl)-1-[2-(oxiran-2-ylmethoxy)phenyl]propan-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

文献信息

• Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study
  作者：Branka M. Ivković、Katarina Nikolic、Bojana B. Ilić、Željko S. Žižak、Radmila B. Novaković、Olivera A. Čudina、Sote M. Vladimirov

  DOI：10.1016/j.ejmech.2013.02.013

  日期：2013.5

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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.