(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide | 1122596-74-0

• 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: (4R,4aR,7S,7aR,12bS)-7-hydroxy-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide
• CAS: 1122596-74-0
• 化学式: C₂₀H₂₂N₂O₃
• 分子量: 338.406
• InChiKey: UHTVVDCKOSRQTI-WORIJJMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R,4aR,7S,7aR,12bS)-3-allyl-7-hydroxy-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carbonitrile 在 氢氧化钾 、 水 作用下， 以 叔丁醇 为溶剂， 生成 (4R,4aR,7S,7aR,12bS)-7-hydroxy-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-9-carboxamide
  参考文献：
  名称：

  Syntheses and opioid receptor binding properties of carboxamido-substituted opioids

  摘要：

  A series of 15 novel opioid derivatives were made where the prototypic phenolic-OH group of traditional opioids was replaced by a carboxamido (CONH2) group. For 2,6-methano-3-benzazocines and morphinans similar or, in a few instances, enhanced affinity for mu, delta and kappa opioid receptors was observed when the OH --> CONH2 switch was applied. For 4,5 alpha-epoxymorphinans, binding affinities for the corresponding carboxamide derivatives were much lower than the OH partner consistent with our pharmacophore hypothesis concerning carboxamide bioactive conformation. The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.134

文献信息

• US20140275545A1
  申请人：——

  公开号：US20140275545A1

  公开（公告）日：2014-09-18
• 8-CARBOXAMIDO-2,6-METHANO-3-BENZAZOCINES
  申请人：Rensselaer Polytechnic Institute

  公开号：US20170217977A1

  公开（公告）日：2017-08-03

  8-Substituted-2,6-methano-3-benzazocines of general structure I in which A is —CH 2 —OH, —CH 2 NH 2 , —NHSO 2 CH 3 , and Y is O, S or NOH are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications. 8-Carboxamides, thiocarboxamides, hydroxyamidines and formamides are preferred.
• Syntheses and opioid receptor binding properties of carboxamido-substituted opioids
  作者：Mark P. Wentland、Rongliang Lou、Qun Lu、Yigong Bu、Melissa A. VanAlstine、Dana J. Cohen、Jean M. Bidlack

  DOI：10.1016/j.bmcl.2008.10.134

  日期：2009.1

  A series of 15 novel opioid derivatives were made where the prototypic phenolic-OH group of traditional opioids was replaced by a carboxamido (CONH2) group. For 2,6-methano-3-benzazocines and morphinans similar or, in a few instances, enhanced affinity for mu, delta and kappa opioid receptors was observed when the OH --> CONH2 switch was applied. For 4,5 alpha-epoxymorphinans, binding affinities for the corresponding carboxamide derivatives were much lower than the OH partner consistent with our pharmacophore hypothesis concerning carboxamide bioactive conformation. The active metabolite of tramadol and its carboxamide counterpart had comparable affinities for the three receptors. (C) 2008 Elsevier Ltd. All rights reserved.