phenylmethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-4-phenyl-1H-pyrrole-3-carboxylate | 135833-78-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: phenylmethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-4-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: benzyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-5-(4-fluorophenyl)-4-phenyl-2-propan-2-ylpyrrole-3-carboxylate
• CAS: 135833-78-2
• 化学式: C₃₂H₃₂FNO₄
• 分子量: 513.609
• InChiKey: NGXYEEFMMKOOEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  49.69
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenylmethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-4-phenyl-1H-pyrrole-3-carboxylate 在 盐酸 、 水 、 对甲苯磺酸 作用下， 反应 24.0h， 生成 5-(4-Fluoro-phenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid benzyl 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：

  2-(2-氨乙基)-1,3-二氧戊环 在 sodium hydroxide 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 9.0h， 生成 phenylmethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-5-(4-fluorophenyl)-2-(1-methylethyl)-4-phenyl-1H-pyrrole-3-carboxylate
  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

文献信息

• ROTH, B. D.;BLANKLEY, C. J.;CHUCHOLOWSKI, A. W.;FERGUSON, E.;HOEFLE, M. L+, J. MED. CHEM., 34,(1991) N, C. 357-366
  作者：ROTH, B. D.、BLANKLEY, C. J.、CHUCHOLOWSKI, A. W.、FERGUSON, E.、HOEFLE, M. L+

  DOI：——

  日期：——