Episalvinorin B | 862073-85-6

• 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: Episalvinorin B
• 英文别名: C-8-epi-salvinorin B；8-epi-salvinorin B；(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester；methyl (2S,4aS,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 862073-85-6
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: BLTMVAIOAAGYAR-FDENTGNSSA-N

物化性质

• 沸点：
  562.8±50.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Episalvinorin B 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 SALVINORINB(品牌:CAYMAN进口)
  参考文献：
  名称：

  Asymmetric Synthesis of Salvinorin A, A Potent κ Opioid Receptor Agonist

  摘要：

  The stereoselective synthesis of salvinorin A is described. A macrocyclic bis-Michael reaction cascade provides the requisite tricyclic skeleton as a single diastereomer.

  DOI：

  10.1021/ja073590a
• 作为产物：
  描述：

  在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 甲醇 、 正己烷 、 丙酮 、 苯 为溶剂， 反应 0.75h， 生成 Episalvinorin B
  参考文献：
  名称：

  Asymmetric Synthesis of Salvinorin A, A Potent κ Opioid Receptor Agonist

  摘要：

  The stereoselective synthesis of salvinorin A is described. A macrocyclic bis-Michael reaction cascade provides the requisite tricyclic skeleton as a single diastereomer.

  DOI：

  10.1021/ja073590a

文献信息

• Opioid receptor ligands and methods for their preparation
  申请人：Prisinzano Thomas

  公开号：US20060058264A1

  公开（公告）日：2006-03-16

  The invention provides novel compounds of formula I: that are opioid receptor ligands. The invention also provides pharmaceutical compositions comprising such compounds as well as methods for treating diseases associated with opioid receptor function by administering such compounds to a mammal in need of treatment. The invention also provides an improved method for isolating intermediate materials useful for obtaining compounds of formula I.

  该发明提供了公式I的新化合物，这些化合物是阿片受体配体。该发明还提供了包含这些化合物的药物组合物，以及通过向需要治疗的哺乳动物施用这些化合物来治疗与阿片受体功能相关的疾病的方法。该发明还提供了一种改进的方法，用于分离中间体材料，以获得公式I的化合物。
• Neoclerodane Diterpenes as a Novel Scaffold for μ Opioid Receptor Ligands
  作者：Wayne W. Harding、Kevin Tidgewell、Nathan Byrd、Howard Cobb、Christina M. Dersch、Eduardo R. Butelman、Richard B. Rothman、Thomas E. Prisinzano

  DOI：10.1021/jm048963m

  日期：2005.7.1

  Structural modification of salvinorin A, the active component of Salvia divinorum, has resulted in the synthesis of novel neoclerodane diterpenes with opioid receptor affinity and activity. We report in this study a nonnitrogenous neoclerodane diterpene with mu opioid receptor affinity (13) that is an agonist at mu opioid receptors. This represents the identification of a novel structural class of

  Salvinorin A（Salvia divinorum的活性成分）的结构修饰已导致合成了具有阿片受体亲和力和活性的新型新环戊烷二萜。我们在这项研究中报告了一种非氮新环戊二烯双萜，具有μ阿片受体的亲和力（13），是μ阿片受体的激动剂。这代表了对μ阿片样物质受体激动剂的新型结构类别的鉴定。
• Development of an Enzyme Immunoassay Using a Monoclonal Antibody against the Psychoactive Diterpenoid Salvinorin A
  作者：Madan Kumar Paudel、Osamu Shirota、Kaori Sasaki-Tabata、Hiroyuki Tanaka、Setsuko Sekita、Satoshi Morimoto

  DOI：10.1021/np400358n

  日期：2013.9.27

  Salvinorin A (1), the main active constituent in Salvia divinorum, is a highly selective kappa-opioid receptor agonist with hallucinogenic effects, which is regulated in several countries. In the present study, a monoclonal antibody (mAb) against 1 was prepared, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) system was developed for the detection of salvinorins. To raise mAbs against 1, salvinorin B (2) hemisuccinate was synthesized and used to prepare the immunogen 2-bovine serum albumin conjugate. This technique was used to prepare a hybridoma cell line, 3D5, which secreted a rnAb that recognized 1. The mAb was shown to have specificity for 1 and other salvinorins in cross-reactivity tests. The intra-assay calibration range by icELISA using the mAb against 1 was 0.0195-0.625 mu g/mL. After validating the icELISA using intra- and interassays, a recovery experiment and analysis of several plants in the family Lamiaceae, including S. divinorum, confirmed that the analytical method based on ELISA is not only simple but also precise, accurate, sensitive, and sufficiently reliable. The results indicate that icELISA is a useful tool in the identification of S. divinorum.
• Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)
  作者：Cécile Béguin、Michele R. Richards、Yulin Wang、Yong Chen、Lee-Yuan Liu-Chen、Zhongze Ma、David Y.W. Lee、William A. Carlezon、Bruce M. Cohen

  DOI：10.1016/j.bmcl.2005.03.113

  日期：2005.6

  Salvinorin A is the only known non-nitrogenous and specific K-opioid agonist. A series of salvinorin A derivatives were prepared and tested for in vitro activity at the K-opioid receptor. Unsubstituted carbamate 9 was a potent K-agonist (EC50 = 6.2 nM) and should be more stable than salvinorin A toward metabolic transformations. Compound 10, containing an N-methyl carbamate at C(2), showed partial agonist activity with 81% efficacy when compared with the full agonist U50,488H. No antagonist ligands were observed. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues
  作者：David Y.W. Lee、Vishnu V.R. Karnati、Minsheng He、Lee-Yuan Liu-Chen、Leelakrishna Kondaveti、Zhongze Ma、Yulin Wang、Yong Chen、Cecile Beguin、William A. Carlezon、Bruce Cohen

  DOI：10.1016/j.bmcl.2005.05.048

  日期：2005.8

  Salvinorin A is the most potent naturally occurring opioid agonist yet discovered with high selectivity and affinity for kappa-opioid receptor. To explore its structure and activity relationships, a series of salvinorin A derivatives modified at the C(2) position were prepared and studied. These salvinorin A derivatives were screened for binding and functional activities at the human K-opioid receptor. Compound 4, containing a methoxymethyl group at the 2-position, was a full kappa-agonist with an EC50 value at 0.6 nM, which is about 7 times more potent than salvinorin A. (c) 2005 Elsevier Ltd. All rights reserved.