methyl (1S,2R,4S,10R,11R,13S,17R)-4-(furan-3-yl)-2,10-dimethyl-6-oxo-15-sulfanylidene-5,14,16-trioxatetracyclo[8.7.0.02,7.013,17]heptadecane-11-carboxylate | 844841-23-2

• 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: methyl (1S,2R,4S,10R,11R,13S,17R)-4-(furan-3-yl)-2,10-dimethyl-6-oxo-15-sulfanylidene-5,14,16-trioxatetracyclo[8.7.0.02,7.013,17]heptadecane-11-carboxylate
• CAS: 844841-23-2
• 化学式: C₂₂H₂₆O₇S
• 分子量: 434.51
• InChiKey: TZLZSQNQGCMFTL-LVWQHBLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4S,10R,11R,13S,17R)-4-(furan-3-yl)-2,10-dimethyl-6-oxo-15-sulfanylidene-5,14,16-trioxatetracyclo[8.7.0.02,7.013,17]heptadecane-11-carboxylate 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.5h， 生成 (-)-1-Deoxosalvinorin A
  参考文献：
  名称：

  Studies toward the Pharmacophore of Salvinorin A, a Potent κ Opioid Receptor Agonist

  摘要：

  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.

  DOI：

  10.1021/jm049438q
• 作为产物：
  描述：

  丹酚 A 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 methyl (1S,2R,4S,10R,11R,13S,17R)-4-(furan-3-yl)-2,10-dimethyl-6-oxo-15-sulfanylidene-5,14,16-trioxatetracyclo[8.7.0.02,7.013,17]heptadecane-11-carboxylate
  参考文献：
  名称：

  Studies toward the Pharmacophore of Salvinorin A, a Potent κ Opioid Receptor Agonist

  摘要：

  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.

  DOI：

  10.1021/jm049438q

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.