(2R)-trans-4-<<(1,1-dimethylethyl)silyl>oxy>-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-2H-pyran-2-one | 135911-87-4

• 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-4-<<(1,1-dimethylethyl)silyl>oxy>-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-2H-pyran-2-one
• 英文别名: (4R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[2-[2-(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]ethyl]oxan-2-one
• CAS: 135911-87-4
• 化学式: C₂₆H₃₈FNO₃Si
• 分子量: 459.677
• InChiKey: UTOIVYSNYBECMB-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-trans-4-<<(1,1-dimethylethyl)silyl>oxy>-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-2H-pyran-2-one 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-{2-[3,4-dichloro-2-(4-fluoro-phenyl)-5-isopropyl-pyrrol-1-yl]-ethyl}-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：

  trans-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到(2R)-trans-4-<<(1,1-dimethylethyl)silyl>oxy>-6-<2-<2-(4-fluorophenyl)-5-(1-methylethyl)-1H-pyrrol-1-yl>ethyl>tetrahydro-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：——