Dibromo-12-epi-salvinorin A | 1232837-66-9

• 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: Dibromo-12-epi-salvinorin A
• 英文别名: 15,16-dibromo-12-epi-salvinorin；13,16-dibromo-12-epi-salvinorin A；methyl (2R,4aR,6aR,7R,9S,10aS,10bR)-9-acetyloxy-2-(2,5-dibromofuran-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 1232837-66-9
• 化学式: C₂₃H₂₆Br₂O₈
• 分子量: 590.263
• InChiKey: USTSOTFFGSVWIP-LNYQLWRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  12-epi-Salvinorin A 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以31%的产率得到Dibromo-12-epi-salvinorin A
  参考文献：
  名称：

  [EN] SALVINORIN DERIVATIVES AND USES THEREOF
  [FR] DÉRIVÉS DE SALVINORINE ET LEURS UTILISATIONS

  摘要：

  该发明涉及选择性作用于κ阿片受体的salvinorin组合物；利用选择性κ受体激动剂治疗躁狂症的方法；以及利用salvinorin组合物治疗情绪障碍，如抑郁障碍和躁狂障碍的方法。

  公开号：

  WO2010075045A1

文献信息

• Differential signaling properties at the kappa opioid receptor of 12-epi-salvinorin A and its analogues
  作者：Cécile Béguin、Justin Potuzak、Wei Xu、Lee-Yuan Liu-Chen、John M. Streicher、Chad E. Groer、Laura M. Bohn、William A. Carlezon、Bruce M. Cohen

  DOI：10.1016/j.bmcl.2011.11.128

  日期：2012.1

  The kappa opioid receptor (KOPR) has been identified as a potential drug target to prevent or alter the course of mood, anxiety and addictive disorders or reduce response to stress. In a search for highly potent and selective KOPR partial agonists as pharmacological tools, we have modified 12-epi-salvinorin A, a compound which we have previously observed to be a KOPR partial agonist. Five analogues of 12-epi-salvinorin A were synthesized and their effects on G protein activation as well as beta-arrestin2 recruitment were evaluated. Only 12-epi-salvinorin A (1) partially activated signaling through G proteins, yet acted as a full agonist in the beta-arrestin 2 DiscoveRx assay. Other salvinorin analogues tested in these functional assays were full agonists in both assays of KOPR activation. By comparison, the non-selective opioid ligand nalbuphine, known to be a partial agonist for G-protein activation, was also a partial agonist for the beta-arrestin mediated signaling pathway activated through KOPR. (C) 2011 Elsevier Ltd. All rights reserved.