6,7-didehydro-3-methoxy-17-methyl-5'-trifluoromethylquinolino[2',3':6,7]morphinan-14β-ol | 1403209-73-3

• 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: 6,7-didehydro-3-methoxy-17-methyl-5'-trifluoromethylquinolino[2',3':6,7]morphinan-14β-ol
• CAS: 1403209-73-3
• 化学式: C₂₆H₂₅F₃N₂O₂
• 分子量: 454.492
• InChiKey: VZGCTDOTNVYRQV-UBFVSLLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.59
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,7-didehydro-3-methoxy-17-methyl-5'-trifluoromethylquinolino[2',3':6,7]morphinan-14β-ol 在 盐酸 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 (1R,14S,15R)-25-methyl-9-(trifluoromethyl)-4,25-diazahexacyclo[13.7.3.01,14.03,12.05,10.017,22]pentacosa-3,5,7,9,11,17(22),18,20-octaene-14,20-diol;hydrochloride
  参考文献：
  名称：

  Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

  摘要：

  We have reported previously the novel delta opioid agonist KNT-127 which showed high affinity and selectivity for the delta receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical delta agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5'-, 6'-, 7'- or 8'-position of the quinoline ring and revealed that many derivatives with 5'- or 8'-substituents showed high affinities and selectivities for the delta receptor. Especially, SYK-153 with an 8'-OH group showed the highest affinity and the most balanced and highest selectivity for the delta receptor among the synthesized compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.004
• 作为产物：
  描述：

  在 盐酸 、 lithium aluminium tetrahydride 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,1,2,2-四氯乙烷 为溶剂， 反应 3.0h， 生成 6,7-didehydro-3-methoxy-17-methyl-5'-trifluoromethylquinolino[2',3':6,7]morphinan-14β-ol
  参考文献：
  名称：

  Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

  摘要：

  We have reported previously the novel delta opioid agonist KNT-127 which showed high affinity and selectivity for the delta receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical delta agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5'-, 6'-, 7'- or 8'-position of the quinoline ring and revealed that many derivatives with 5'- or 8'-substituents showed high affinities and selectivities for the delta receptor. Especially, SYK-153 with an 8'-OH group showed the highest affinity and the most balanced and highest selectivity for the delta receptor among the synthesized compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.004