6,7-didehydro-5'-(N,N-dimethylamino)-17-methylquinolino[2',3':6,7]morphinan-3,14β-diol | 1403210-39-8

• 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-5'-(N,N-dimethylamino)-17-methylquinolino[2',3':6,7]morphinan-3,14β-diol
• 英文别名: (1R,14S,15R)-9-(dimethylamino)-25-methyl-4,25-diazahexacyclo[13.7.3.01,14.03,12.05,10.017,22]pentacosa-3,5(10),6,8,11,17(22),18,20-octaene-14,20-diol
• CAS: 1403210-39-8
• 化学式: C₂₆H₂₉N₃O₂
• 分子量: 415.535
• InChiKey: YDBVSUOIZSLTTQ-TWJOJJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  59.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-didehydro-5'-(N,N-dimethylamino)-17-methylquinolino[2',3':6,7]morphinan-3,14β-diol 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 以78%的产率得到(1R,14S,15R)-9-(dimethylamino)-25-methyl-4,25-diazahexacyclo[13.7.3.01,14.03,12.05,10.017,22]pentacosa-3,5(10),6,8,11,17(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：

  2-amino-6-nitrobenzaldehyde 在 盐酸 、 聚合甲醛 、 甲烷磺酸 、 sodium cyanoborohydride 作用下， 以 乙醇 、 溶剂黄146 、 乙腈 、 三氟乙酸 为溶剂， 反应 63.0h， 生成 6,7-didehydro-5'-(N,N-dimethylamino)-17-methylquinolino[2',3':6,7]morphinan-3,14β-diol
  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

文献信息

• Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
  作者：Yoshihiro Ida、Ayaka Matsubara、Toru Nemoto、Manabu Saito、Shigeto Hirayama、Hideaki Fujii、Hiroshi Nagase

  DOI：10.1016/j.bmc.2012.08.004

  日期：2012.10

  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.