17-benzyl-6,7-didehydro-3-methoxy-quinolino[2',3':6,7]morphinan | 1357173-07-9

• 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: 17-benzyl-6,7-didehydro-3-methoxy-quinolino[2',3':6,7]morphinan
• CAS: 1357173-07-9
• 化学式: C₃₁H₃₀N₂O
• 分子量: 446.592
• InChiKey: QJOIKIFVLRCYII-LXLYTFERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  25.36
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17-benzyl-6,7-didehydro-3-methoxy-quinolino[2',3':6,7]morphinan 在 三溴化硼 、 氨 、 水 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到17-benzyl-6,7-didehydro-quinolino[2',3':6,7]morphinan-3-ol
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047
• 作为产物：
  描述：

  (4b'S,8a'R,9′R)-3′-methoxy-8′,8a',9′,10′-tetrahydro-5′H,7′Hspiro[[1,3]dioxolane-2,6′-[9,4b](epiminoethano)phenanthrene] 在 盐酸 、 甲烷磺酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 17-benzyl-6,7-didehydro-3-methoxy-quinolino[2',3':6,7]morphinan
  参考文献：
  名称：

  Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists

  摘要：

  The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the delta opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the 8 receptor over the mu receptor than the corresponding SN-28 derivatives with the 3-hydroxy group (SN-11, 23, 28). Derivatives with the 4-hydroxy group showed potent agonist activities for the 5 receptor in the [S-35]GTPyS binding assay. Although the 17-cyclopropylmethyl derivative (SN-11) with a 3-hydroxy group showed the lowest selectivity for the delta receptor among the morphinan derivatives, the agonist activity toward the delta receptor was the most potent for candidates with the 3-hydroxy group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.047