N-vanillyl-9-octadecynamide | 96513-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-vanillyl-9-octadecynamide
• 英文别名: 9-Octadecynamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-；N-[(4-hydroxy-3-methoxyphenyl)methyl]octadec-9-ynamide
• CAS: 96513-74-5
• 化学式: C₂₆H₄₁NO₃
• 分子量: 415.616
• InChiKey: BBRZZCYVWKZJJY-UHFFFAOYSA-N

物化性质

• 沸点：
  598.5±50.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  硬脂炔酸 在 草酰氯 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-vanillyl-9-octadecynamide
  参考文献：
  名称：

  香草。1.具有抗伤害感受和抗炎活性的辣椒素类似物。

  摘要：

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。

  DOI：

  10.1021/jm00070a002

文献信息

• Compounds and compositions useful for producing analgesia
  申请人：The Procter & Gamble Company

  公开号：US04532139A1

  公开（公告）日：1985-07-30

  Alkynamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R is straight or branched alkyne having from 11 to 23 carbon atoms; R.sub.1 is H, OH, or OCH.sub.3 ; R.sub.2 is OH or a short-chain ester; and wherein at least one of R.sub.1 and R.sub.2 is OH or OCH.sub.3. Compositions, useful for producing analgesia in humans or lower animals, comprise a safe and effective amount of: an alkynamide, pharmaceutically-acceptable salts thereof, or mixtures thereof; and a pharmaceutically-acceptable carrier. Preferably, these alkynamides are N-vanillyl-alkynamides. Methods of treatment, comprising administering a safe and effective amount of these alkynamides, pharmaceutically-acceptable salts thereof, or mixtures thereof, include methods of parenteral, oral, and topical administration.

  翻译结果如下： 炔胺化合物及其药学上可接受的盐的化学式为：##STR1## 其中X为O或S; R为直链或支链炔烃，碳原子数为11到23个; R.sub.1为H，OH或OCH.sub.3; R.sub.2为OH或短链酯; 至少其中一个为OH或OCH.sub.3。这些炔胺化合物组成的配方，可用于人类或动物的镇痛，包括安全有效的量：炔胺、其药学上可接受的盐，或其混合物; 以及药学上可接受的载体。最好是N-香草基炔胺。治疗方法包括经皮、口服和局部给药的方法，其中包括给予安全有效量的这些炔胺化合物、其药学上可接受的盐或其混合物。
• Pharmaceutical products providing enhanced analgesia
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0149544A2

  公开（公告）日：1985-07-24

  An analgesic composition comprising capsaicin or a capsaicin analog and an analgesic selected from the class of opioids is disclosed. This combination has been found to exhibit unexpectedly enhanced analgesic activity in humans and lower animals without a corresponding increase in undesirable side effects.

  本研究公开了一种镇痛组合物，它由辣椒素或辣椒素类似物和一种选自阿片类的镇痛剂组成。研究发现，这种组合物在人类和低等动物中的镇痛活性出乎意料地增强，而不良副作用却没有相应增加。
• <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.
• JANUSZ, J. M.;LAHANN, T. R.
  作者：JANUSZ, J. M.、LAHANN, T. R.

  DOI：——

  日期：——
• Novel compounds and compositions useful for producing analgesia
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0132114B1

  公开（公告）日：1986-09-24