N-cyclopropylmethyl-14β-[4'-chlorophenylpropioloylamino]-7,8-dihydronorcodeinone | 1195777-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-cyclopropylmethyl-14β-[4'-chlorophenylpropioloylamino]-7,8-dihydronorcodeinone
• 英文别名: N-Cyclopropylmethyl-14beta-[4''-chlorophenylpropioloylamino]-7,8-dihydronorcodeinone；N-[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-methoxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-chlorophenyl)prop-2-ynamide
• CAS: 1195777-24-2
• 化学式: C₃₀H₂₉ClN₂O₄
• 分子量: 517.024
• InChiKey: CDKZODPLDWSATB-QVDUQQMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-cyclopropylmethyl-14β-[4'-chlorophenylpropioloylamino]-7,8-dihydronorcodeinone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到N-cyclopropylmethyl-14β-[4'-chlorophenylpropioloylamino]-7,8-dihydronormorphinone
  参考文献：
  名称：

  14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

  摘要：

  14 beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.

  DOI：

  10.1021/jm901074a
• 作为产物：
  描述：

  3-(4-chlorophenyl)propioloyl chloride 、 14-amino dihydrocodeinone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以27%的产率得到N-cyclopropylmethyl-14β-[4'-chlorophenylpropioloylamino]-7,8-dihydronorcodeinone
  参考文献：
  名称：

  14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists

  摘要：

  14 beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.

  DOI：

  10.1021/jm901074a

文献信息

• 14β-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and Related Opioids. Further Examples of Pseudoirreversible μ Opioid Receptor Antagonists
  作者：Nick P.R. Nieland、David Rennison、Jillian H. Broadbear、Lauren Purington、James H. Woods、John R. Traynor、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm901074a

  日期：2009.11.12

  14 beta-4'-Chlorocinnamoylaminodihydronormorphinone (2a), and analogues, are selective pseudoirreversible antagonists of the mu opioid receptor (MOR). The preparation of analogues with ethynic bonds, replacing the ethenic bond of 2a, is described. The new ligands, in mouse antinociceptive assays, had pseudoirreversible MOR antagonist activity, which, in the case of 8b was of longer duration than that of 2a. The related codeinone (9b) had only antagonist activity in vivo, in contrast to 2a's codeinone equivalent 3a, which had potent antinociceptive activity.