N-(adamantan-1-yl)-8-butoxy-2-oxo-2H-chromene-3-carboxamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(adamantan-1-yl)-8-butoxy-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(1-adamantyl)-8-butoxy-2-oxo-2H-benzopyran-3-carboxamide；N-(1-adamantyl)-8-butoxy-2-oxochromene-3-carboxamide
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: AYRVGOBUOADVRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-butoxy-2-hydroxybenzaldehyde 在 哌啶 、 氯化亚砜 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 N-(adamantan-1-yl)-8-butoxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Design, syntheses, structure–activity relationships and docking studies of coumarin derivatives as novel selective ligands for the CB2 receptor

  摘要：

  The CB2 receptor has been considered as an inspiring drug target for the treatment of pain and immune-related diseases. In the current manuscript, a novel series of coumarin derivatives is reported to be designed and synthesized by combining the structural features of some known ligands for the cannabinoid receptors based on the CoMFA model of the lead compounds. The compounds were evaluated to be highly selective ligands for the CB2 receptor over the CBI receptor by calcium mobilization assays. Furthermore, SAR results indicate that the functionality of a ligand is controlled by the substituent on the nucleus. Therefore, molecular docking simulations were performed to calculate the receptor-ligand interactions of our synthesized compounds binding to the CB2 receptor. The understanding of the binding modes could be advantageous for further development of selective ligands for the CB2 receptor. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.054