4-<2'-chloro-4'-methyl-5'-<2-(ethoxycarbonyl)ethyl>phenyl>-4-oxobutyric acid | 108579-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-<2'-chloro-4'-methyl-5'-<2-(ethoxycarbonyl)ethyl>phenyl>-4-oxobutyric acid
• 英文别名: 4-(2-Chloro-4-methyl-5'-ethoxycarbonylethyl-phenyl)-4-oxobutyric acid；4-[2-chloro-5-(3-ethoxy-3-oxopropyl)-4-methylphenyl]-4-oxobutanoic acid
• CAS: 108579-14-2
• 化学式: C₁₆H₁₉ClO₅
• 分子量: 326.777
• InChiKey: QCFAWRZGUDGQLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-<2'-chloro-4'-methyl-5'-<2-(ethoxycarbonyl)ethyl>phenyl>-4-oxobutyric acid 在 盐酸 、 草酰氯 、 四氯化锡 、 锌 作用下， 以 二氯甲烷 、 乙酸酐 、 甲苯 为溶剂， 反应 149.0h， 生成 ethyl 3-(4-chloro-2-methyl-8-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)propanoate
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 6. trans-6-[2-(Substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones

  摘要：

  A variety of trans-6-[2-(substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones were prepared and, upon conversion to their 3,5-dihydroxy carboxylates, were found to have good inhibitory activity against the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase, the rate-determining enzyme in cholesterogenesis. The most active compounds are 2,4,6- and 2,4,7-trichloro derivatives and would be expected to display about the same potency as the standard compactin upon resolution.

  DOI：

  10.1021/jm00164a047
• 作为产物：
  描述：

  3-(4-chloro-2-methylphenyl)propionic acid 在 三氯化铝 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 30.5h， 生成 4-<2'-chloro-4'-methyl-5'-<2-(ethoxycarbonyl)ethyl>phenyl>-4-oxobutyric acid
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 6. trans-6-[2-(Substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones

  摘要：

  A variety of trans-6-[2-(substituted-1-naphthyl)ethyl(or ethenyl)]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-ones were prepared and, upon conversion to their 3,5-dihydroxy carboxylates, were found to have good inhibitory activity against the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase, the rate-determining enzyme in cholesterogenesis. The most active compounds are 2,4,6- and 2,4,7-trichloro derivatives and would be expected to display about the same potency as the standard compactin upon resolution.

  DOI：

  10.1021/jm00164a047

文献信息

• Synthetic analogs of mevinolin
  申请人：Merck & Co., Inc.

  公开号：US04654363A1

  公开（公告）日：1987-03-31

  Certain 6-(substituted-naphthyl)hydrocarbyl-4-hydroxytetrahydropyran-2-ones are unexpectedly potent in the treatment of familial hypercholesterolemia, hyperlipemia and atherosclerosis by virtue of their ability to inhibit the enzyme, 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase).

  某些6-(取代萘基)烃基-4-羟基四氢吡喃-2-酮类化合物因其抑制酶3-羟基-3-甲基戊二酰辅酶A还原酶（HMG-CoA还原酶）的能力，在治疗家族性高胆固醇血症、高脂血症和动脉粥样硬化方面具有出乎意料的强效作用。
• PRUGH, J. D.
  作者：PRUGH, J. D.

  DOI：——

  日期：——
• US4654363A
  申请人：——

  公开号：US4654363A

  公开（公告）日：1987-03-31