dimethyl 2-(4-fluorophenyl)-5-(1-methylethyl)-1-(3-oxopropyl)-1H-pyrrole-3,4-dicarboxylate | 104568-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 2-(4-fluorophenyl)-5-(1-methylethyl)-1-(3-oxopropyl)-1H-pyrrole-3,4-dicarboxylate
• 英文别名: Dimethyl 2-(4-fluorophenyl)-1-(3-oxopropyl)-5-propan-2-ylpyrrole-3,4-dicarboxylate
• CAS: 104568-96-9
• 化学式: C₂₀H₂₂FNO₅
• 分子量: 375.397
• InChiKey: AQBBZUAPIQXYPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4-fluorophenyl)-5-(1-methylethyl)-1-(3-oxopropyl)-1H-pyrrole-3,4-dicarboxylate 生成 2-(4-Fluoro-phenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-5-isopropyl-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 1-<2-(1,3-dioxolan-2-yl)ethyl>-2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrole-3,4-dicarboxylate 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以90%的产率得到dimethyl 2-(4-fluorophenyl)-5-(1-methylethyl)-1-(3-oxopropyl)-1H-pyrrole-3,4-dicarboxylate
  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：——
• ——
  作者：HOEFLE M. L.、 ROTH B. D.、 STRATTON C. D.

  DOI：——

  日期：——
• 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
  作者：Bruce D. Roth、C. J. Blankley、A. W. Chucholowski、E. Ferguson、M. L. Hoefle、D. F. Ortwine、R. S. Newton、C. S. Sekerke、D. R. Sliskovic、M Wilson

  DOI：10.1021/jm00105a056

  日期：1991.1

  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.