1-(2-[1,3]Dioxolan-2-yl-ethyl)-2-(4-fluoro-phenyl)-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester | 135833-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-[1,3]Dioxolan-2-yl-ethyl)-2-(4-fluoro-phenyl)-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester
• 英文别名: diethyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-2-(4-fluorophenyl)-5-propan-2-ylpyrrole-3,4-dicarboxylate
• CAS: 135833-90-8
• 化学式: C₂₄H₃₀FNO₆
• 分子量: 447.504
• InChiKey: FXHBPNCIMIKFMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.99
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(2-[1,3]Dioxolan-2-yl-ethyl)-2-(4-fluoro-phenyl)-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以95%的产率得到2-(4-Fluoro-phenyl)-5-isopropyl-1-(3-oxo-propyl)-1H-pyrrole-3,4-dicarboxylic acid diethyl ester
  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 N-(4-fluorobenzoyl)-N-<2-(2-ethyl)-1,3-dioxolanyl>valine 在 sodium hydroxide 、 乙酸酐 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 1-(2-[1,3]Dioxolan-2-yl-ethyl)-2-(4-fluoro-phenyl)-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester
  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