thiophene-2-carboxylic acid (2S,4aS,6aR,7R,9S,10aS,10bR)-7-carbomethoxy-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-9-yl ester | 901309-99-7

• 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: thiophene-2-carboxylic acid (2S,4aS,6aR,7R,9S,10aS,10bR)-7-carbomethoxy-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-9-yl ester
• 英文别名: thiophene-2-carboxylic acid (2S,4aR,6aR,7R,9S,10aS,10bR)-7-carbomethoxy-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-9-yl ester；methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(thiophene-2-carbonyloxy)-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 901309-99-7
• 化学式: C₂₆H₂₈O₈S
• 分子量: 500.57
• InChiKey: BZNOPGMFTTXDTR-KBJPRCPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-噻吩甲酰氯 、 SALVINORINB(品牌:CAYMAN进口) 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到thiophene-2-carboxylic acid (2S,4aS,6aR,7R,9S,10aS,10bR)-7-carbomethoxy-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-9-yl ester
  参考文献：
  名称：

  Salvinorin A类似物作为阿片受体探针的合成。

  摘要：

  最近已证明几种新环戊烷类化合物，例如沙威诺林A（1）和赫金诺林（3）在体外和体内均具有阿片样物质受体的活性。为了探索这种有趣的化合物类别的结构亲和力关系，我们合成了一系列从Salvia divinorum分离的1种类似物。在这里，我们报告新环戊烷二萜的半合成及其在阿片受体上的结构亲和力关系。这项工作将允许进一​​步开发新型阿片受体配体。

  DOI：

  10.1021/np060094b

文献信息

• Synthesis of Salvinorin A Analogues as Opioid Receptor Probes
  作者：Kevin Tidgewell、Wayne W. Harding、Anthony Lozama、Howard Cobb、Kushal Shah、Pavitra Kannan、Christina M. Dersch、Damon Parrish、Jeffrey R. Deschamps、Richard B. Rothman、Thomas E. Prisinzano

  DOI：10.1021/np060094b

  日期：2006.6.1

  Several neoclerodanes, such as salvinorin A (1) and herkinorin (3), have recently been shown to possess opioid receptor activity in vitro and in vivo. To explore the structure-affinity relationships of this interesting class of compounds, we have synthesized a series of analogues from 1 isolated from Salvia divinorum. Here, we report the semisynthesis of neoclerodane diterpenes and their structure-affinity

  最近已证明几种新环戊烷类化合物，例如沙威诺林A（1）和赫金诺林（3）在体外和体内均具有阿片样物质受体的活性。为了探索这种有趣的化合物类别的结构亲和力关系，我们合成了一系列从Salvia divinorum分离的1种类似物。在这里，我们报告新环戊烷二萜的半合成及其在阿片受体上的结构亲和力关系。这项工作将允许进一​​步开发新型阿片受体配体。
• WO2006/138589
  申请人：——

  公开号：——

  公开（公告）日：——
• Herkinorin Analogues with Differential β-Arrestin-2 Interactions
  作者：Kevin Tidgewell、Chad E. Groer、Wayne W. Harding、Anthony Lozama、Matthew Schmidt、Alfred Marquam、Jessica Hiemstra、John S. Partilla、Christina M. Dersch、Richard B. Rothman、Laura M. Bohn、Thomas E. Prisinzano

  DOI：10.1021/jm701162g

  日期：2008.4.1

  Salvinorin A is a psychoactive natural product that has been found to be a potent and selective kappa opioid receptor agonist in vitro and in vivo. The activity of salvinorin A is unusual compared to other opioids such as morphine in that it mediates potent kappa opioid receptor signaling yet leads to less receptor downregulation than observed with other kappa agonists. Our initial chemical modifications of salvinorin A have yielded one analogue, herkinorin (1c), with high affinity at the mu OR. We recently reported that 1c does not promote the recruitment of beta-arrestin-2 to the mu OR or receptor internalization. Here we describe three new derivatives of 1c (3c, 3f, and 3i) with similar properties and one, benzamide 7b, that promotes recruitment of beta-arrestin-2 to the mu OR and receptor internalization. When the important role mu opioid receptor regulation plays in determining physiological responsiveness to opioid narcotics is considered,mu opioids derived from salvinorin A may offer a unique template for the development of functionally selective mu opioid receptor-ligands with the ability to produce analgesia while limiting adverse side effects.