摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

1-(3-hydroxy-3-cyclohexylpropyl)-3(R*),4(R*)-dimethyl-4-(3-hydroxyphenyl)piperidine

中文名称
——
中文别名
——
英文名称
1-(3-hydroxy-3-cyclohexylpropyl)-3(R*),4(R*)-dimethyl-4-(3-hydroxyphenyl)piperidine
英文别名
3-[1-(3-Cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenol;3-[(3R,4R)-1-(3-cyclohexyl-3-hydroxypropyl)-3,4-dimethylpiperidin-4-yl]phenol
1-(3-hydroxy-3-cyclohexylpropyl)-3(R<sup>*</sup>),4(R<sup>*</sup>)-dimethyl-4-(3-hydroxyphenyl)piperidine化学式
CAS
——
化学式
C22H35NO2
mdl
——
分子量
345.525
InChiKey
LVVHEFJXPXAUDD-QNGGVGCWSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    N,N,N-trimethyl-3-cyclohexyl-3-oxopropanaminium iodide 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 1-(3-hydroxy-3-cyclohexylpropyl)-3(R*),4(R*)-dimethyl-4-(3-hydroxyphenyl)piperidine
    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
点击查看最新优质反应信息

文献信息

  • 3,4-Dimethyl-4-(3-hydroxyphenyl)piperidines: opioid antagonists with potent anorectant activity
    作者:Charles H. Mitch、J. David Leander、Laurane G. Mendelsohn、Walter N. Shaw、David T. Wong、Buddy E. Cantrell、Bryan G. Johnson、John K. Reel、John D. Snoddy
    DOI:10.1021/jm00072a002
    日期:1993.10
    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.
查看更多