azelaic acid vanillamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: azelaic acid vanillamide
• 英文别名: azelayl vanillamide；N,N'-bis(4-hydroxy-3-methoxybenzyl)nonanediamide；N,N'-bis[(4-hydroxy-3-methoxyphenyl)methyl]nonanediamide
• 化学式: C₂₅H₃₄N₂O₆
• 分子量: 458.555
• InChiKey: UZFONCZIVNMQPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  壬二酸 、 香兰素胺盐酸盐 在 propylphosphonic anhydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到azelaic acid vanillamide
  参考文献：
  名称：

  N-Acylvanillamides:  Development of an Expeditious Synthesis and Discovery of New Acyl Templates for Powerful Activation of the Vanilloid Receptor

  摘要：

  A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be. substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropAnation, while omega dimerization led to a substantial increase of activity. Because of the Wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.

  DOI：

  10.1021/jm020844o

文献信息

• USE OF N-ACYLVANILLINAMIDE DERIVATIVES AS AGONISTS OF PERIPHERAL CANNABINOID CB1 RECEPTORS
  申请人：Innovet Italia S.r.l.

  公开号：EP1115392B1

  公开（公告）日：2002-12-11
• N-acylvanillinamide derivatives capable of activating peripheral cannabinoid receptors
  申请人：Bisogno Tiziana

  公开号：US20050065216A1

  公开（公告）日：2005-03-24

  The present invention relates to the use of N-acylvanillinamide derivatives capable of activating the peripheral receptor CB1 of cannabinoids. In particular, the present invention relates to the use of compounds of general formula (I) in which the meanings of R, R 1 , R 3 and Y are as defined in the description, for the preparation of a medicinal product which is capable of activating the peripheral receptor CB1 of cannabinoids.
• US7244767B2
  申请人：——

  公开号：US7244767B2

  公开（公告）日：2007-07-17
• <i>N</i>-Acylvanillamides:  Development of an Expeditious Synthesis and Discovery of New Acyl Templates for Powerful Activation of the Vanilloid Receptor
  作者：Giovanni Appendino、Alberto Minassi、Aniello Schiano Morello、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1021/jm020844o

  日期：2002.8.1

  A simple and general synthesis of vanillamides was developed and employed to screen acids from the fatty and isoprenoid pools for new acyl templates of biological relevance as capsaicin analogues. Potent activation of the human vanilloid receptor 1 (VR1) was observed for the vanillamides of certain polyfunctional acids from both pools, showing that the vanilloid activity of capsaicinoids can be. substantially improved by introducing polar groups and/or unsaturations on the acyl moiety. The activity of the unsaturated analogues was maintained or even increased by cyclopropAnation, while omega dimerization led to a substantial increase of activity. Because of the Wide structural diversity of the library of compounds screened, these observations could not be translated into a single framework of structure-activity relationships. Nevertheless, a series of new highly active leads was identified, validating the pharmacological potential of the unnatural combination of natural building blocks to provide new bioactive compounds.