<(-)-isopinocampheyl> 4-pyridylacetate | 130276-09-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: <(-)-isopinocampheyl> 4-pyridylacetate
• 英文别名: [(1R,2R,3R,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl] 2-pyridin-4-ylacetate
• CAS: 130276-09-4
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: FYHFPSGWNXSFBI-FAAHXZRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-4-乙酸甲酯 、 (-)-异松蒎醇 在 正丁基锂 作用下， 生成 <(-)-isopinocampheyl> 4-pyridylacetate
  参考文献：
  名称：

  Inhibition of enzymes of estrogen and androgen biosynthesis by esters of 4-pyridylacetic acid

  摘要：

  A variety of esters of 4-pyridylacetic acid have been prepared by base mediated exchange from the methyl ester. Several of the esters of alcohols that contained a cyclohexyl ring were potent inhibitors of human placental aromatase and of the rat testicular 17 alpha-hydroxylase/C17-20lyase complex. The most potent agents found against both enzyme complexes were the borneyl, isopinocampheyl, and 1-adamantyl esters. These were over 100 times more potent than aminoglutethimide against aromatase and of greater potency than ketoconazole against hydroxylase/lyase. Potency against either enzyme complex was reduced if the ester function was borne on the cyclohexyl ring in an axial rather than an equatorial position. Some differential selectivity could be introduced since whereas methyl substitution adjacent to the carbonyl group reduced the inhibition of aromatase, it increased that against hydroxylase/lyase.

  DOI：

  10.1021/jm00173a022