LY 255610

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: LY 255610
• 英文别名: (+)-1-<3(R)-3-hydroxy-3-cyclohexylpropyl>-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine；3-[(3R,4R)-1-[(3R)-3-cyclohexyl-3-hydroxypropyl]-3,4-dimethylpiperidin-4-yl]phenol
• 化学式: C₂₂H₃₅NO₂
• 分子量: 345.525
• InChiKey: LVVHEFJXPXAUDD-MTNREXPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R,4R)-3,4-二甲基-4-(3-羟基苯基)哌啶 在 sodium tetrahydroborate 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.0h， 生成 LY 255610
  参考文献：
  名称：

  3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity

  摘要：

  A series of (3R*,4R*)-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists with varying substituents on the nitrogen were evaluated for their effect on food consumption in obese Zucker rats. Opioid affinity (mu, kappa, and delta for selected compounds) and opioid antagonist activity (mu and kappa) were characterized and compared to effects on food consumption. No compounds with high selectivity for either mu or kappa receptors were discovered. However, compounds in the series had exceptional potency as opioid antagonists and in reducing food consumption in the obese Zucker rat. In contrast, a few compounds with high potency as opioid antagonists had much weaker potency for inhibiting food consumption. (3R,4R)-3,4-Dimethyl-1-[(3S)-3-hydroxy-3-cyclohexyl-propyl]-4-(3-hydroxyphenyl)piperidine(11,LY255582)emerged as having the best activity profile, both in reducing food consumption and as an opioid antagonist. Compound 11 is a highly potent mu, kappa-, and delta-opioid antagonist with possible clinical utility as an appetite suppressant for weight loss.

  DOI：

  10.1021/jm00072a002