Retvanil

• 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: Retvanil
• 英文别名: (2E,4E,6E,8E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• 化学式: C₂₈H₃₇NO₃
• 分子量: 435.607
• InChiKey: FGFIMXXLJAZRKO-IGHSUZHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  维A酸 、 香兰素胺盐酸盐 在 氰基磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到Retvanil
  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

• VR1 VANILLOID RECEPTOR ANTAGONISTS WITH A IONONIC SUBSTRUCTURE
  申请人：Pharmeste S.r.l.

  公开号：EP2046752B1

  公开（公告）日：2010-05-19
• US7919624B2
  申请人：——

  公开号：US7919624B2

  公开（公告）日：2011-04-05
• [EN] VR1 VANILLOID RECEPTOR ANTAGONISTS WITH A IONONIC SUBSTRUCTURE<br/>[FR] ANTAGONISTES DU RÉCEPTEUR VANILLOÏDE VR1 DOTÉS D'UNE SOUS-STRUCTURE IONONIQUE
  申请人：PHARMESTE SRL

  公开号：WO2008006481A1

  公开（公告）日：2008-01-17

  [EN] The invention provides compounds of formula (I), wherein Y, R, n and X are as defined in the description, a process for their preparation and pharmaceutical compositions containing them. The compounds of formula (I) inhibit the Transient Receptor Potential Vanilloid 1 (TRPV1 ), which plays a pivotal role in the development of post-inflammatory analgesia, therefore they can be used as analgesic and anti-inflammatory drugs.
  [FR] La présente invention se rapporte à des composés représentés par la formule (I), dans laquelle Y, R, n et X sont tels que définis dans la description, à un procédé permettant de les préparer et à des compositions pharmaceutiques les contenant. Les composés représentés par la formule (I) inhibent le récepteur vanilloïde TRPV1 (Transient Receptor Potential Vanilloid 1), qui joue un rôle central dans le développement de l'analgésie post-inflammatoire, et peuvent donc servir de médicaments analgésiques et anti-inflammatoires.
• <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.