(2R)-trans-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-trifluoroacetyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-4-hydroxy-2H-pyran-2-one | 135833-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2R)-trans-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-trifluoroacetyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-4-hydroxy-2H-pyran-2-one
• 英文别名: 6-{2-[2-(4-Fluoro-phenyl)-5-isopropyl-3-(2,2,2-trifluoro-acetyl)-pyrrol-1-yl]-ethyl}-4-hydroxy-tetrahydro-pyran-2-one；(4R,6R)-6-[2-[2-(4-fluorophenyl)-5-propan-2-yl-3-(2,2,2-trifluoroacetyl)pyrrol-1-yl]ethyl]-4-hydroxyoxan-2-one
• CAS: 135833-87-3
• 化学式: C₂₂H₂₃F₄NO₄
• 分子量: 441.423
• InChiKey: RKUYYDQPUDHAJE-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-{2-[2-(4-fluoro-phenyl)-5-isopropyl-3-(2,2,2-trifluoro-acetyl)-pyrrol-1-yl]-ethyl}-tetrahydro-pyran-2-one 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (2R)-trans-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-3-trifluoroacetyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-4-hydroxy-2H-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

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：——