tert-butyl (3R,5S)-7-(5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-isopropyl-1H-pyrazol-3-yl)-3,5-dihydroxyheptanoate | 1005475-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl (3R,5S)-7-(5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-isopropyl-1H-pyrazol-3-yl)-3,5-dihydroxyheptanoate
• 英文别名: tert-butyl (3R,5R)-7-[5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate
• CAS: 1005475-70-6
• 化学式: C₃₁H₄₀FN₃O₅
• 分子量: 553.674
• InChiKey: KECFOKQVYKPGBA-JWQCQUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R,5S)-7-(5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-isopropyl-1H-pyrazol-3-yl)-3,5-dihydroxyheptanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以97%的产率得到(3R,5R)-7-(5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-isopropyl-1H-pyrazol-3-yl)-3,5-dihydroxyheptanoic acid sodium salt
  参考文献：
  名称：

  Substituted Pyrazoles as Hepatoselective HMG-CoA Reductase Inhibitors: Discovery of (3R,5R)-7-[2-(4-Fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic Acid (PF-3052334) as a Candidate for the Treatment of Hypercholesterolemia

  摘要：

  In light of accumulating evidence that aggressive LDL-lowering therapy may offer increased protection against coronary heart disease, we undertook the design and synthesis of a novel series of HMG-CoA reductase inhibitors based upon a substituted pyrazole template. Optimizing this series using both structure-based design and molecular property considerations afforded a class of highly efficacious and hepatoselective inhibitors resulting in the identification of (3 R,5 R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2 H-pyrazol-3-yl]-3,5-dihydroxy-heptanoic (PF-3052334) as a candidate for the treatment of hypercholesterolemia.

  DOI：

  10.1021/jm070849r
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以56%的产率得到tert-butyl (3R,5S)-7-(5-(benzylcarbamoyl)-1-(4-fluorophenyl)-4-isopropyl-1H-pyrazol-3-yl)-3,5-dihydroxyheptanoate
  参考文献：
  名称：

  Substituted Pyrazoles as Hepatoselective HMG-CoA Reductase Inhibitors: Discovery of (3R,5R)-7-[2-(4-Fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic Acid (PF-3052334) as a Candidate for the Treatment of Hypercholesterolemia

  摘要：

  In light of accumulating evidence that aggressive LDL-lowering therapy may offer increased protection against coronary heart disease, we undertook the design and synthesis of a novel series of HMG-CoA reductase inhibitors based upon a substituted pyrazole template. Optimizing this series using both structure-based design and molecular property considerations afforded a class of highly efficacious and hepatoselective inhibitors resulting in the identification of (3 R,5 R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2 H-pyrazol-3-yl]-3,5-dihydroxy-heptanoic (PF-3052334) as a candidate for the treatment of hypercholesterolemia.

  DOI：

  10.1021/jm070849r