17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-hydroxy-6,7:2',3'-indolomorphinan

• 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-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-hydroxy-6,7:2',3'-indolomorphinan
• 英文别名: (1S,2R,13R,21R)-22-(cyclopropylmethyl)-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaen-16-ol
• 化学式: C₂₆H₂₆N₂O₂
• 分子量: 398.505
• InChiKey: IYMLCJZYVKMKSH-YCULYRLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二氢可待因酮 在 盐酸 、 氯甲酸乙烯酯 、 三溴化硼 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 63.5h， 生成 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-hydroxy-6,7:2',3'-indolomorphinan
  参考文献：
  名称：

  14-Desoxy Analogues of Naltrindole and 7-Spiroindanyloxymorphone:  The Role of the 14-Hydroxy Group at δ Opioid Receptors

  摘要：

  The 14-hydroxy group is known to increase the antagonist potency of mu-selective opioid ligands. To investigate the role of this group at the delta opioid receptor, the 14-desoxy analogues (7 and 9) of the delta-selective ligands, naltrindole (1, NTI) and spiroindanyloxymorphone (2, SIOM), have been synthesized and tested. The in vitro pharmacologic activities of 7 and 9 suggest that the 14-hydroxy group plays an important role in determining the delta selectivity and potency of NTI and SIOM.

  DOI：

  10.1021/jm980209b

文献信息

• CARBOXAMIDE BIOISOSTERES OF OPIATES
  申请人：Rensselaer Polytechnic Institute

  公开号：US20130225628A1

  公开（公告）日：2013-08-29

  A compound of formula I is disclosed. Compounds of formula I are useful as analgesics, anti-inflammatory agents, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.
• 4-HYDROXYBENZOMORPHANS
  申请人：Rensselaer Polytechnic Institute

  公开号：US20150011768A1

  公开（公告）日：2015-01-08

  4-Hydroxybenzomorphans containing carboxamide or thiocarboxamide at the 3-position are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.
• US8716306B2
  申请人：——

  公开号：US8716306B2

  公开（公告）日：2014-05-06
• 14-Desoxy Analogues of Naltrindole and 7-Spiroindanyloxymorphone:  The Role of the 14-Hydroxy Group at δ Opioid Receptors
  作者：Tushar A. Kshirsagar、Xinqin Fang、Philip S. Portoghese

  DOI：10.1021/jm980209b

  日期：1998.7.1

  The 14-hydroxy group is known to increase the antagonist potency of mu-selective opioid ligands. To investigate the role of this group at the delta opioid receptor, the 14-desoxy analogues (7 and 9) of the delta-selective ligands, naltrindole (1, NTI) and spiroindanyloxymorphone (2, SIOM), have been synthesized and tested. The in vitro pharmacologic activities of 7 and 9 suggest that the 14-hydroxy group plays an important role in determining the delta selectivity and potency of NTI and SIOM.