Salvinorinyl-2-propionate | 689295-71-4

• 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-propionate
• 英文别名: (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(propionyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester；methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-propanoyloxy-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 689295-71-4
• 化学式: C₂₄H₃₀O₈
• 分子量: 446.497
• InChiKey: UPFVFWZGNRKYFG-ZWLNRFIDSA-N

物化性质

• 熔点：
  217-221 °C
• 沸点：
  573.4±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  乙腈：1mg/mL； DMF：2mg/mL； DMF:PBS(pH 7.2)(1:1)：0.5 mg/ml；二甲基亚砜：1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  丹酚 A 在 4-二甲氨基吡啶 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Salvinorinyl-2-propionate
  参考文献：
  名称：

  Neoclerodane diterpenes作为新型阿片类阿片受体配体的支架。

  摘要：

  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。

  DOI：

  10.1021/jm048963m

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。
• Salvinorin A, an Active Component of the Hallucinogenic Sage <i>Salvia divinorum</i> Is a Highly Efficacious κ-Opioid Receptor Agonist: Structural and Functional Considerations
  作者：Charles Chavkin、Sumit Sud、Wenzhen Jin、Jeremy Stewart、Jordan K. Zjawiony、Daniel J. Siebert、Beth Ann Toth、Sandra J. Hufeisen、Bryan L. Roth

  DOI：10.1124/jpet.103.059394

  日期：2004.3

  The diterpene salvinorin A from Salvia divinorum has recently been reported to be a high-affinity and selective kappa-opioid receptor agonist (Roth et al., 2002). Salvinorin A and selected derivatives were found to be potent and efficacious agonists in several measures of agonist activity using cloned human kappa-opioid receptors expressed in human embryonic kidney-293 cells. Thus, salvinorin A, s

  最近已经报道了来自Salvia divinorum的二萜salvinorin A是一种高亲和力的选择性κ阿片受体激动剂（Roth等，2002）。使用在人胚胎肾293细胞中表达的克隆的人κ阿片受体，在几种激动剂活性的量度中，发现Salvinorin A和选定的衍生物是有效的激动剂。因此，发现salvinorin A，salvinorinyl-2-丙酸酯和salvinorinyl-2-庚酸酯是完全的（salvinorin A）或部分的（2-丙酸酯，2-庚酸酯）激动剂，用于抑制福斯高林刺激的cAMP产生。通过共转染嵌合G蛋白Gaq-i5或通用G蛋白Ga16并定量激动剂引起的细胞内钙动员，对Salvinorin A的激动剂效能和功效进行了其他研究，申明萨尔维诺林A是有效且有效的κ阿片类激动剂。结构功能研究的结果表明，Salvinorin A的2位上的取代基的性质对于κ阿片受体的结合和激活至关重要。
• 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.
• US7728001B2
  申请人：——

  公开号：US7728001B2

  公开（公告）日：2010-06-01