2-geranyl-3,5-dimethoxy-3′,4′-dihydroxy-(E)-stilbene | 1542214-40-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-geranyl-3,5-dimethoxy-3′,4′-dihydroxy-(E)-stilbene
• 英文别名: 4-[(E)-2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-dimethoxyphenyl]ethenyl]benzene-1,2-diol
• CAS: 1542214-40-3
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: ZJLYXDXTIMOVSI-ALYWKMAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-geranyl-3,5-dimethoxy-3′,4′-dihydroxy-(E)-stilbene 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以27%的产率得到2-geranyl-3,5,3′,4′-tetramethoxy-(E)-stilbene
  参考文献：
  名称：

  Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists

  摘要：

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.

  DOI：

  10.1021/np4009046
• 作为产物：
  描述：

  (E)-2-((2-(3,7-dimethylocta-2,6-dien-1-yl)-3,5-dimethoxybenzyl)oxy)tetrahydro-2H-pyran 在 manganese(IV) oxide 、 15-冠醚-5 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 mineral oil 为溶剂， 反应 2.5h， 生成 2-geranyl-3,5-dimethoxy-3′,4′-dihydroxy-(E)-stilbene
  参考文献：
  名称：

  Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists

  摘要：

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.

  DOI：

  10.1021/np4009046

文献信息

• Stilbenes as κ-Selective, Non-nitrogenous Opioid Receptor Antagonists
  作者：Alyssa M. Hartung、John A. Beutler、Hernán A. Navarro、David F. Wiemer、Jeffrey D. Neighbors

  DOI：10.1021/np4009046

  日期：2014.2.28

  The natural stilbene pawhuskin A has been shown to function as an opioid receptor antagonist, with preferential binding to the kappa receptor. This finding encouraged assembly of a set of analogues to probe the importance of key structural features. Assays on these compounds determined that one (compound 29) shows potent opioid receptor binding activity and significantly improved selectivity for the kappa receptor. These studies begin to illuminate the structural features of these non-nitrogenous opioid, receptor antagonists that are required for activity.