N-cyclopropylmethyl-14-amino-3-deoxymorphinone | 301152-35-2

• 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-14-amino-3-deoxymorphinone
• 英文别名: (4R,4aS,7aR,12bR)-4a-amino-3-(cyclopropylmethyl)-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• CAS: 301152-35-2
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: XNJYOEKVLKMVMV-BTHPGYMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-氯苯基)丙烯酰氯 、 N-cyclopropylmethyl-14-amino-3-deoxymorphinone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以62%的产率得到3-Deoxyclocinnamox
  参考文献：
  名称：

  3-Deoxyclocinnamox:  The First High-Affinity, Nonpeptide μ-Opioid Antagonist Lacking a Phenolic Hydroxyl Group

  摘要：

  The C-3-substituent in morphinan opioids is of critical importance; the 3-OH group is usually associated with very much higher affinity for mu-receptors than H or -OMe. However in this series of 14 beta-cinnamoylamino derivatives the codeinones (e.g. methoclocinnamox, MC-CAM) had unexpectedly high mu-opioid receptor affinity, similar to that of the morphinone (clocinnamox, C-CAM). The current report relates to the synthesis and in vitro evaluation of deoxyclocinnamox (DOC-CAM) which acted as a high-affinity opioid antagonist similar to C-CAM but with greater mu selectivity. Thus it appears that the C-3-substituent does not play a major role in the binding of the 14 beta-cinnamoyl series and that the cinnamoyl group itself may in fact be the dominant binding feature.

  DOI：

  10.1021/jm0009641
• 作为产物：
  描述：

  N-cyclopropylmethyl-14-formamidocodeinone 在 10percent Pd/C 盐酸 、 氢气 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -30.0~20.0 ℃ 、310.27 kPa 条件下， 反应 100.0h， 生成 N-cyclopropylmethyl-14-amino-3-deoxymorphinone
  参考文献：
  名称：

  3-Deoxyclocinnamox:  The First High-Affinity, Nonpeptide μ-Opioid Antagonist Lacking a Phenolic Hydroxyl Group

  摘要：

  The C-3-substituent in morphinan opioids is of critical importance; the 3-OH group is usually associated with very much higher affinity for mu-receptors than H or -OMe. However in this series of 14 beta-cinnamoylamino derivatives the codeinones (e.g. methoclocinnamox, MC-CAM) had unexpectedly high mu-opioid receptor affinity, similar to that of the morphinone (clocinnamox, C-CAM). The current report relates to the synthesis and in vitro evaluation of deoxyclocinnamox (DOC-CAM) which acted as a high-affinity opioid antagonist similar to C-CAM but with greater mu selectivity. Thus it appears that the C-3-substituent does not play a major role in the binding of the 14 beta-cinnamoyl series and that the cinnamoyl group itself may in fact be the dominant binding feature.

  DOI：

  10.1021/jm0009641

文献信息

• 3-Deoxyclocinnamox:  The First High-Affinity, Nonpeptide μ-Opioid Antagonist Lacking a Phenolic Hydroxyl Group
  作者：Ian Derrick、Claire L. Neilan、Jennifer Andes、Stephen M. Husbands、James H. Woods、John R. Traynor、John W. Lewis

  DOI：10.1021/jm0009641

  日期：2000.8.1

  The C-3-substituent in morphinan opioids is of critical importance; the 3-OH group is usually associated with very much higher affinity for mu-receptors than H or -OMe. However in this series of 14 beta-cinnamoylamino derivatives the codeinones (e.g. methoclocinnamox, MC-CAM) had unexpectedly high mu-opioid receptor affinity, similar to that of the morphinone (clocinnamox, C-CAM). The current report relates to the synthesis and in vitro evaluation of deoxyclocinnamox (DOC-CAM) which acted as a high-affinity opioid antagonist similar to C-CAM but with greater mu selectivity. Thus it appears that the C-3-substituent does not play a major role in the binding of the 14 beta-cinnamoyl series and that the cinnamoyl group itself may in fact be the dominant binding feature.