[(2S,4aR,6aS,7R,9S,10aS,10bR)-2-(furan-3-yl)-7-(hydroxymethyl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromen-9-yl] acetate | 844841-22-1

• 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: [(2S,4aR,6aS,7R,9S,10aS,10bR)-2-(furan-3-yl)-7-(hydroxymethyl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromen-9-yl] acetate
• CAS: 844841-22-1
• 化学式: C₂₂H₂₈O₇
• 分子量: 404.46
• InChiKey: VGXFIZVZRKZEGJ-XNRHGJAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,4aR,6aS,7R,9S,10aS,10bR)-2-(furan-3-yl)-7-(hydroxymethyl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromen-9-yl] acetate 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到[(2S,4aR,6aS,7R,9S,10aS,10bR)-7-formyl-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromen-9-yl] acetate
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.08.051
• 作为产物：
  描述：

  丹酚 A 在 硼烷四氢呋喃络合物 、 lithium iodide 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 38.0h， 生成 [(2S,4aR,6aS,7R,9S,10aS,10bR)-2-(furan-3-yl)-7-(hydroxymethyl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromen-9-yl] acetate
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.08.051

文献信息

• Studies toward the Pharmacophore of Salvinorin A, a Potent κ Opioid Receptor Agonist
  作者：Thomas A. Munro、Mark A. Rizzacasa、Bryan L. Roth、Beth A. Toth、Feng Yan

  DOI：10.1021/jm049438q

  日期：2005.1.1

  Salvinorin A (1), from the sage Salvia divinorum, is a potent and selective K opioid receptor (KOR) agonist. We screened other salvinorins and derivatives for binding affinity and functional activity at opioid receptors. Our results suggest that the methyl ester and furan ring are required for activity but that the lactone and ketone functionalities are not. Other salvinorins showed negligible binding affinity at the KOR. None of the compounds bound to mu or delta opioid receptors.
• 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.
• 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.