(1S,2S,6R,14R,15R)-18-[4-(dimethylamino)phenyl]-11-hydroxy-15-methoxy-5-methyl-13-oxa-5,18-diazaheptacyclo[13.5.2.12,8.01,6.02,14.016,20.012,23]tricosa-8(23),9,11,21-tetraene-17,19-dione

• 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: (1S,2S,6R,14R,15R)-18-[4-(dimethylamino)phenyl]-11-hydroxy-15-methoxy-5-methyl-13-oxa-5,18-diazaheptacyclo[13.5.2.12,8.01,6.02,14.016,20.012,23]tricosa-8(23),9,11,21-tetraene-17,19-dione
• 化学式: C₃₀H₃₁N₃O₅
• 分子量: 513.593
• InChiKey: QZXDQSTZCMKQLH-GIASXGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-(dimethylamino)phenyl)-1H-pyrrole-2,5-dione 在 三溴化硼 作用下， 以 氯仿 、 苯 为溶剂， 反应 1.0h， 生成 (1S,2S,6R,14R,15R)-18-[4-(dimethylamino)phenyl]-11-hydroxy-15-methoxy-5-methyl-13-oxa-5,18-diazaheptacyclo[13.5.2.12,8.01,6.02,14.016,20.012,23]tricosa-8(23),9,11,21-tetraene-17,19-dione
  参考文献：
  名称：

  Synthesis and pharmacological activity of thebaine-derived μ-opioid receptor agonists

  摘要：

  Thebaine-derived mu-opioid agonists were synthesized through the reaction of thebaine with N-aryl maleimide and tested for opioid activity. Morphine was used as reference compound. Our results show that an attachment of aryl succinimide group to thebaine produced series of compounds with mu-opioid agonist activity. The most active compound in smooth muscle preparation was compound 6 with an IC50 ratio of delta/mu = 248.69 and was as potent as morphine with ED50 value 26.65 mg kg-1 i.p. in hot-plate test and showed good antinociceptive activity.

  DOI：

  10.1016/s0031-6865(98)00031-4

文献信息

• Synthesis and pharmacological activity of thebaine-derived μ-opioid receptor agonists
  作者：A. Shafiee、M. Amanlou、H. Farsam、A.R. Dehpour、F. Mir-Ershadi、A.R. Mani

  DOI：10.1016/s0031-6865(98)00031-4

  日期：1999.2

  Thebaine-derived mu-opioid agonists were synthesized through the reaction of thebaine with N-aryl maleimide and tested for opioid activity. Morphine was used as reference compound. Our results show that an attachment of aryl succinimide group to thebaine produced series of compounds with mu-opioid agonist activity. The most active compound in smooth muscle preparation was compound 6 with an IC50 ratio of delta/mu = 248.69 and was as potent as morphine with ED50 value 26.65 mg kg-1 i.p. in hot-plate test and showed good antinociceptive activity.