1'-benzyl-17-cyclopropylmethyl-6,7-dedihydro-3,14-dihydroxy-4,5α-epoxy-5'-methyl-4'-phenylpyrrolo[2',3':6,7]morphinan

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 1'-benzyl-17-cyclopropylmethyl-6,7-dedihydro-3,14-dihydroxy-4,5α-epoxy-5'-methyl-4'-phenylpyrrolo[2',3':6,7]morphinan
• 英文别名: (1S,2S,9R,17R)-7-benzyl-18-(cyclopropylmethyl)-6-methyl-5-phenyl-10-oxa-7,18-diazahexacyclo[9.9.1.01,9.02,17.04,8.015,21]henicosa-4(8),5,11,13,15(21)-pentaene-2,12-diol
• 化学式: C₃₆H₃₆N₂O₃
• 分子量: 544.693
• InChiKey: XKUPUVJJRUFEFD-FHPDIGCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  纳曲酮 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 1'-benzyl-17-cyclopropylmethyl-6,7-dedihydro-3,14-dihydroxy-4,5α-epoxy-5'-methyl-4'-phenylpyrrolo[2',3':6,7]morphinan
  参考文献：
  名称：

  4‘-Arylpyrrolomorphinans:  Effect of a Pyrrolo-N-benzyl Substituent in Enhancing δ-Opioid Antagonist Activity

  摘要：

  A new method for the preparation of N-benzylpyrrolomorphinans has been developed. Thus Michael reaction of the benzylimines of oxycodones and oxymorphones with nitrostyrenes gave a series of 4'-aryl-N-benzylpyrrolomorphinans. These were selective delta antagonists of much higher in vitro potency (with 5a having K-e delta = <1 nM) than their binding affinities predicted. In mice in vivo assays 5a showed good delta antagonist activity in the antiwrithing analgesic assay and also inhibited delta agonist-induced convulsant activity.

  DOI：

  10.1021/jm010841w