(3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-trifluoromethanesulfonyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester | 910305-46-3

• 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: (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-trifluoromethanesulfonyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester
• CAS: 910305-46-3
• 化学式: C₂₂H₂₅F₃O₉S
• 分子量: 522.496
• InChiKey: VZSFIQILUUMAKS-CEFSSPBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  126.18
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-trifluoromethanesulfonyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester 在 sodium azide 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (3S,4aR,4bS,6R,8R,8aR,10aR)-6-Amino-3-furan-3-yl-4a,8a-dimethyl-1,5-dioxo-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and in vitro evaluation of salvinorin A analogues: Effect of configuration at C(2) and substitution at C(18)

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.05.093
• 作为产物：
  描述：

  丹酚 A 在 吡啶 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (3S,4aR,4bS,6S,8R,8aR,10aR)-3-Furan-3-yl-4a,8a-dimethyl-1,5-dioxo-6-trifluoromethanesulfonyloxy-dodecahydro-2-oxa-phenanthrene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and in vitro pharmacological evaluation of salvinorin A analogues modified at C(2)

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.03.113