4-{2-[4-(5-Hydroxy-5-methyl-hexyl)-phenyl]-ethyl}-4-methyl-cyclohexanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-{2-[4-(5-Hydroxy-5-methyl-hexyl)-phenyl]-ethyl}-4-methyl-cyclohexanol
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: ACLUTGGMNKIXIY-AQYVVDRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-氯苯基磷酸二乙酯 在 palladium on activated charcoal 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 31.0 ℃ 、275.79 kPa 条件下， 反应 54.25h， 生成 4-{2-[4-(5-Hydroxy-5-methyl-hexyl)-phenyl]-ethyl}-4-methyl-cyclohexanol
  参考文献：
  名称：

  Design and Synthesis of Seco-oxysterol Analogs as Potential Inhibitors of 3-Hydroxy-3-methylglutaryl-Coenzyme A (HMG-CoA) Reductase Gene Transcription

  摘要：

  The synthesis and biological activity of a series of seco-oxysterol analogs designed to be inhibitors of transcription of the gene for 3-hydroxy-3-methylglutaryl-Coenzyme A reductase (HMGR) are described. The compound possessing the most significant activity, [1 alpha(E),4 beta]-3-[2-(4-hydroxy- 1-methylcyclohexyl)ethenyl]-alpha,alpha-dimethylbenzenepentanol (4, U-88156), inhibited (IC50 = 10 mu M) the expression of beta-galactosidase (beta-gal) in a transfected human HepG2 cell line wherein the beta-gal gene was driven by a 5 kB segment of the promoter for hamster HMGR. Furthermore, using wild-type HepG2 cells, it was shown that 10 mu M: 4 reduced HMGR mRNA levels by 73% while stimulating LDL-receptor activity by 47%. In the same system, the related oxysterol, 25-hydroxycholesterol (1), at 10 mu M lowered both HMGR mRNA levels and LDL-receptor activity by 58% and 64%, respectively. Overall HMGR activity in wild-type HepG2 cells was inhibited 30% by 4 at 10 mu M. These findings collectively demonstrate that a secooxysterol analog is capable of regulating HMGR gene expression and that this regulation can occur without a concomitant attenuation of the level of LDL-receptor activity.

  DOI：

  10.1021/jm00041a013