4-(4-Fluoro-phenyl)-2-isopropyl-5-methyl-1H-pyrrole-3-carboxylic acid ethyl ester | 188557-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-(4-Fluoro-phenyl)-2-isopropyl-5-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
• CAS: 188557-35-9
• 化学式: C₁₇H₂₀FNO₂
• 分子量: 289.35
• InChiKey: SYYOABJJIQIAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-2-isopropyl-5-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 在 四丙基高钌酸铵 、 4 A molecular sieve 、 sodium hydride 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 4-(4-Fluorophenyl)-3-formyl-2-isopropyl-5-methyl-1-methylsulfonylpyrrole
  参考文献：
  名称：

  Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- and N-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors

  摘要：

  A novel series of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates were synthesized and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Monocalcium bis(+)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulfonylaminopyrimidin)-5-yl]-(3R,5S)-dihydroxy-(E)-6-heptenoate (3a,S-4522) was selected as a candidate for further evaluation. Compound 3a was approximately four times more potent than lovastatin sodium salt (in inhibiting HMG-CoA reductase in vitro (IC50 = 11 nM). Compound 3a was shown to be the most potent cholesterol biosynthesis inhibitor in this series (IC50 = 1.12 nM) in rat isolated hepatocytes; its inhibitory activity was approximately 100 times more potent than pravastatin. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00248-9
• 作为产物：
  描述：

  2-氨基-1-(4-氟苯基)-1-丙酮盐酸盐 、 异丁酰乙酸乙酯 在 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.0h， 以71.2%的产率得到4-(4-Fluoro-phenyl)-2-isopropyl-5-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of Methanesulfonamide Pyrimidine- and N-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-heptenoates, a Novel Series of HMG-CoA Reductase Inhibitors

  摘要：

  A novel series of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates were synthesized and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. Monocalcium bis(+)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulfonylaminopyrimidin)-5-yl]-(3R,5S)-dihydroxy-(E)-6-heptenoate (3a,S-4522) was selected as a candidate for further evaluation. Compound 3a was approximately four times more potent than lovastatin sodium salt (in inhibiting HMG-CoA reductase in vitro (IC50 = 11 nM). Compound 3a was shown to be the most potent cholesterol biosynthesis inhibitor in this series (IC50 = 1.12 nM) in rat isolated hepatocytes; its inhibitory activity was approximately 100 times more potent than pravastatin. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00248-9