(3S,4aR,4bS,6S,8R,8aR,10aS)-6-Acetoxy-3-furan-3-yl-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid | 865438-43-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,4aR,4bS,6S,8R,8aR,10aS)-6-Acetoxy-3-furan-3-yl-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid
• 英文别名: (2S,4aS,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylic acid
• CAS: 865438-43-3
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: JFOYNIOEQMKAOX-REMVLUENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4aR,4bS,6S,8R,8aR,10aS)-6-Acetoxy-3-furan-3-yl-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid 、 环丙基甲胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues

  摘要：

  Salvinorin A is the most potent naturally occurring opioid agonist with a high selectivity and affinity for kappa-opioid receptor. To explore its structure-activity relationships, modifications at the C(4) position have been studied and a series of salvinorin A derivatives were prepared. These C(4)-modified salvinorin A analogues were screened for binding and functional activities at the human kappa-opioid receptor and several potent new agonists have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.092
• 作为产物：
  描述：

  丹酚 A 在 吡啶 、 lithium iodide 作用下， 反应 36.0h， 以39%的产率得到hapten B
  参考文献：
  名称：

  Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues

  摘要：

  Salvinorin A is the most potent naturally occurring opioid agonist with a high selectivity and affinity for kappa-opioid receptor. To explore its structure-activity relationships, modifications at the C(4) position have been studied and a series of salvinorin A derivatives were prepared. These C(4)-modified salvinorin A analogues were screened for binding and functional activities at the human kappa-opioid receptor and several potent new agonists have been identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.092

文献信息

• Synthesis and in vitro pharmacological studies of new C(4)-modified salvinorin A analogues
  作者：David Y.W. Lee、Minsheng He、Lee-Yuan Liu-Chen、Yulin Wang、Jian-Guo Li、Wei Xu、Zhongze Ma、William A. Carlezon、Bruce Cohen

  DOI：10.1016/j.bmcl.2006.08.051

  日期：2006.11

  Salvinorin A, a compound isolated from the plant Salvia divinorum, is a potent and highly selective agonist for the kappa Opioid receptor. For exploration of its structure and activity relationships, further modifications, such as reduction at the C(4) position, have been studied and a series of salvinorin A derivatives were prepared. These C(4) modified salvinorin A analogues were screened for binding and functional activities at the human K-opioid receptor and several new full agonists have been identified. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro pharmacological studies of C(4) modified salvinorin A analogues
  作者：David Y.W. Lee、Minsheng He、Leelakrishna Kondaveti、Lee-Yuan Liu-Chen、Zhongze Ma、Yulin Wang、Yong Chen、Jian-Guo Li、Cecile Beguin、William A. Carlezon、Bruce Cohen

  DOI：10.1016/j.bmcl.2005.06.092

  日期：2005.10

  Salvinorin A is the most potent naturally occurring opioid agonist with a high selectivity and affinity for kappa-opioid receptor. To explore its structure-activity relationships, modifications at the C(4) position have been studied and a series of salvinorin A derivatives were prepared. These C(4)-modified salvinorin A analogues were screened for binding and functional activities at the human kappa-opioid receptor and several potent new agonists have been identified. (c) 2005 Elsevier Ltd. All rights reserved.