Salvinorinyl-2-chloride | 874624-28-9

• 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: Salvinorinyl-2-chloride
• 英文别名: (3S,4aR,4bS,6R,8R,8aR,10aR)-6-Chloro-3-furan-3-yl-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester；methyl (2S,4aR,6aR,7R,9R,10aS,10bR)-9-chloro-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 874624-28-9
• 化学式: C₂₁H₂₅ClO₆
• 分子量: 408.879
• InChiKey: SGNJGRJIPDONNA-GKRPYSMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Salvinorinyl-2-chloride 在 35S-sodium hydrogen sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以44%的产率得到35S-2-thiol salvinorin B
  参考文献：
  名称：

  [EN] AGENTS WITH SELECTIVE K-OPIOID RECEPTOR AFFINITY
  [FR] AGENTS PRESENTANT UNE AFFINITE SELECTIVE POUR LE RECEPTEUR OPIOIDE K

  摘要：

  公开号：

  WO2006012643A3
• 作为产物：
  描述：

  SALVINORINB(品牌:CAYMAN进口) 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以29%的产率得到Salvinorinyl-2-chloride
  参考文献：
  名称：

  Stewart, D. Jeremy; Fahmy, Hesham; Roth, Bryan L., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 4, p. 269 - 275

  摘要：

  DOI：

文献信息

• Synthesis and in vitro evaluation of salvinorin A analogues: Effect of configuration at C(2) and substitution at C(18)
  作者：Cécile Béguin、Michele R. Richards、Jian-Guo Li、Yulin Wang、Wei Xu、Lee-Yuan Liu-Chen、William A. Carlezon、Bruce M. Cohen

  DOI：10.1016/j.bmcl.2006.05.093

  日期：2006.9

  kappa-opioid receptor ligands have raised interest for their apparent effects on mood. The potent and selective kappa-agonist salvinorin A has short-lasting (15 min) depressive-like effects in rats in behavioral models used to study mood disorders. Two series of salvinorin derivatives modified at C(2) and C(18), respectively, were synthesized and their kappa-opioid receptor affinities, potencies, and efficacies were evaluated using in vitro receptor binding and biochemical functional assays. Modification at C(2) yielded potent kappa-agonists that are predicted to have improved metabolic stability (14a, 15a) or increased water solubility (10b). Our preliminary SAR study at C(18) suggested that this part of the molecule interacts with a tight lipophilic pocket of the K-receptor. (c) 2006 Elsevier Ltd. All rights reserved.
• Stewart, D. Jeremy; Fahmy, Hesham; Roth, Bryan L., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 4, p. 269 - 275
  作者：Stewart, D. Jeremy、Fahmy, Hesham、Roth, Bryan L.、Yan, Feng、Zjawiony, Jordan K.

  DOI：——

  日期：——
• US7687538B2
  申请人：——

  公开号：US7687538B2

  公开（公告）日：2010-03-30
• [EN] AGENTS WITH SELECTIVE K-OPIOID RECEPTOR AFFINITY<br/>[FR] AGENTS PRESENTANT UNE AFFINITE SELECTIVE POUR LE RECEPTEUR OPIOIDE K
  申请人：UNIV MISSISSIPPI

  公开号：WO2006012643A3

  公开（公告）日：2006-06-22
• Convenient synthesis and in vitro pharmacological activity of 2-thioanalogs of salvinorins A and B
  作者：Ruslan V. Bikbulatov、Feng Yan、Bryan L. Roth、Jordan K. Zjawiony

  DOI：10.1016/j.bmcl.2007.01.100

  日期：2007.4

  To study drug-receptor interactions, new thio-derivatives of salvinorin A, an extremely potent natural kappa-opioid receptor (KOR) agonist, were synthesized. Obtained compounds were examined for receptor binding affinity. Analogs with the same configuration at carbon atom C-2 as in natural salvinorin A showed higher affinity to KOR than their corresponding epimers. (c) 2007 Elsevier Ltd. All rights reserved.