5-(4-fluorophenyl)-2-(1-methylethyl)-3-phenyl-1H-pyrrole-1-propanal | 135833-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(4-fluorophenyl)-2-(1-methylethyl)-3-phenyl-1H-pyrrole-1-propanal
• 英文别名: 3-[5-(4-fluorophenyl)-3-phenyl-2-propan-2-ylpyrrol-1-yl]propanal
• CAS: 135833-86-2
• 化学式: C₂₂H₂₂FNO
• 分子量: 335.421
• InChiKey: DNVPAUKFWLSZNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酰乙酸乙酯 、 5-(4-fluorophenyl)-2-(1-methylethyl)-3-phenyl-1H-pyrrole-1-propanal 生成 6-{2-[5-(4-Fluoro-phenyl)-2-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus

  摘要：

  A series of trans-tetrahydro-4-hydroxy-6-[2-(2,3,4,5-substituted-1H-pyrrol-1-yl)ethyl]-2H-pyran-2-ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Inhibitory potency was found to increase substantially when substituents were introduced into positions three and four of the pyrrole ring. A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-[(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.

  DOI：

  10.1021/jm00105a056
• 作为产物：
  描述：

  methyl 3-(4-fluorophenyl)-3-oxo-2-(phenylmethylene)propanoate 在 sodium hydroxide 、 2-(2-hydroxyethyl)-3-methyl-4-benzylthiazolium chloride 、 camphor-10-sulfonic acid 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 42.0h， 生成 5-(4-fluorophenyl)-2-(1-methylethyl)-3-phenyl-1H-pyrrole-1-propanal
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 3. Tetrahydro-4-hydroxy-6-[2-(1H-pyrrol-1-yl)ethyl]-2H-pyran 2-one inhibitors of HMG-CoA reductase. 2. Effects of introducing substituents at positions three and four of the pyrrole nucleus

  摘要：

  A series of trans-tetrahydro-4-hydroxy-6-[2-(2,3,4,5-substituted-1H-pyrrol-1-yl)ethyl]-2H-pyran-2-ones and their dihydroxy acids were prepared and tested for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Inhibitory potency was found to increase substantially when substituents were introduced into positions three and four of the pyrrole ring. A systematic exploration of structure-activity relationships at these two positions led to the identification of a compound ((+)-33, (+)-(4R)-trans-2-(4-fluorophenyl)-5-(1-methylethyl)-N,3-diphenyl-1-[(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-4-carboxamide) with five times the inhibitory potency of the fungal metabolite compactin.

  DOI：

  10.1021/jm00105a056