simvastatin | 79902-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: simvastatin
• 英文别名: [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylpropanoate
• CAS: 79902-39-9
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: VOBAOLPIGHOVNW-INTXDZFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷氧基)-6-[2-(8-羟基-2,6-二甲基-1,2,6,7,8,8a-六氢萘)-乙基]-四氢吡喃-2-酮 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 simvastatin
  参考文献：
  名称：

  3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 4. Side-chain ester derivatives of mevinolin

  摘要：

  Modification of the 2(S)-methylbutyryl moiety of mevinolin led to a series of side chain ester derivatives. A systematic exploration of the structure-activity relationships showed that the introduction of an additional aliphatic group on the carbon alpha to the carbonyl group increased potency. This observation led to the synthesis of compound 16, which has about 2.5 times the intrinsic inhibitory activity of mevinolin.

  DOI：

  10.1021/jm00155a040

文献信息

• HAFFMAN, W. F.;SMITH, R. L.;WILLARD, K.
  作者：HAFFMAN, W. F.、SMITH, R. L.、WILLARD, K.

  DOI：——

  日期：——
• HOFFMAN, W. F.;SMITH, R. L.;WILLARD, A. K.
  作者：HOFFMAN, W. F.、SMITH, R. L.、WILLARD, A. K.

  DOI：——

  日期：——
• 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 4. Side-chain ester derivatives of mevinolin
  作者：W. F. Hoffman、A. W. Alberts、P. S. Anderson、J. S. Chen、R. L. Smith、A. K. Willard

  DOI：10.1021/jm00155a040

  日期：1986.5

  Modification of the 2(S)-methylbutyryl moiety of mevinolin led to a series of side chain ester derivatives. A systematic exploration of the structure-activity relationships showed that the introduction of an additional aliphatic group on the carbon alpha to the carbonyl group increased potency. This observation led to the synthesis of compound 16, which has about 2.5 times the intrinsic inhibitory activity of mevinolin.