salvinorin B methoxymethyl ether | 864378-87-0

• 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: salvinorin B methoxymethyl ether
• 英文别名: 2-methoxymethylsalvinorin B；MOM-Sal B；methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-9-(methoxymethoxy)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 864378-87-0
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: KFVUSZPWUZBAPF-AGQYDFLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  salvinorin B methoxymethyl ether 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.05.048
• 作为产物：
  描述：

  丹酚 A 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 salvinorin B methoxymethyl ether
  参考文献：
  名称：

  Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.05.048

文献信息

• Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists
  作者：David Y.W. Lee、Gang Deng、Zhongze Ma、Wei Xu、Lu Yang、Jing Liu、Ronghua Dai、Lee-Yuan Liu-Chen

  DOI：10.1016/j.bmcl.2015.06.092

  日期：2015.10

  The synthesis of a new series of C-2-alkyl-2-methoxymethyl-salvinorin ethers and their binding affinities at kappa-, mu-, and delta-opioid receptors are presented. We have developed a synthesis that enables installation of alkyl-substituents at C-2 while maintaining the integrity of the C-2 methoxymethyl ether and retaining kappa-opioid receptor binding activity. Among these new compounds, 2-methyl-2-methoxymethyl-salvinorin ether (9a) is a potent full agonist at the kappa receptor and shows comparable potency in K-i and EC50 with salvinorin A and U50488H. These C2-alkylated analogs have been identified as full kappa agonists. (C) 2015 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.