Livanil | 16729-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Livanil
• 英文别名: (Z,Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-octadeca-9,12-dienamide；N-vanillyl-9Z,12Z-octadecadienamide；N-vanillyllinoleamide；9,12-Octadecadienamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (Z,Z)-；(9Z,12Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]octadeca-9,12-dienamide
• CAS: 16729-47-8
• 化学式: C₂₆H₄₁NO₃
• 分子量: 415.616
• InChiKey: QLXBKYBHBQBEFT-NQLNTKRDSA-N

物化性质

• 沸点：
  282-286 °C(Press: 0.5 Torr)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (Z,Z)-9,12-十八烷二烯酸二聚物 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 Livanil
  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

• Anti-tumor pharmaceutical composition comprising N-vanillyl fatty acid amide
  申请人：KUREHA CHEMICAL INDUSTRY COMPANY, Limited

  公开号：US20040110844A1

  公开（公告）日：2004-06-10

  The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1): 1 wherein —CO—R group represents a saturated or unsaturated fatty acid residue containing from 14 to 32 carbon atoms. According to the invention, there was provided an anti-tumor pharmaceutical composition comprising a N-vanillyl fatty acid amide which relates to capsaicin wherein the composition has a low side-effect and a high anti-tumor effect, in particular an anti-melanoma effect and an anti-leukemia cell effect; and is very low pungent, stimulatory and preinflammatory effect.

  本发明提供了一种抗肿瘤药物组合物，具有高抗肿瘤效果和低副作用。该抗肿瘤药物组合物包括式（1）中的N-香草酰基脂肪酰胺：其中，—CO—R基团代表含有14至32个碳原子的饱和或不饱和脂肪酸残基。根据本发明，提供了一种抗肿瘤药物组合物，包括一种与辣椒素相关的N-香草酰基脂肪酰胺，该组合物具有低副作用和高抗肿瘤效果，特别是抗黑色素瘤效果和抗白血病细胞效果；且具有非常低的刺激性和预炎症效果。
• 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。
• Anti-tumour pharmaceutical composition comprising N-vanillyl fatty acid amide
  申请人：Kureha Chemical Industry Company, Limited

  公开号：EP1426047A1

  公开（公告）日：2004-06-09

  The present invention provides an anti-tumor pharmaceutical composition having a high anti-tumor effect with low side-effects. The anti-tumor pharmaceutical composition comprises a N-vanillyl fatty acid amide of formula (1):    wherein -CO-R group represents a saturated or unsaturated fatty acid residue containing from 14 to 32 carbon atoms. According to the invention, there is provided an anti-tumor pharmaceutical composition comprising a N-vanillyl fatty acid amide which is related to capsaicin wherein the composition has a low side-effect and a high anti-tumor effect, in particular an anti-melanoma effect and an anti-leukemia cell effect; and has a very low pungency, a stimulatory and a preinflammatory effect.

  本发明提供了一种抗肿瘤药物组合物，其抗肿瘤效果好，副作用小。 该抗肿瘤药物组合物包括式（1）的 N-香草醛脂肪酸酰胺： 其中 -CO-R 基团代表含有 14 至 32 个碳原子的饱和或不饱和脂肪酸残基。 根据本发明，提供了一种抗肿瘤药物组合物，其中包含一种与辣椒素有关的 N-香草醇脂肪酸酰胺，该组合物具有低副作用和高抗肿瘤效果，特别是抗黑色素瘤效果和抗白血病细胞效果；并且具有极低的辛辣味、刺激和预炎效果。
• Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads
  作者：Hung The Dang、Gyeoung Jin Kang、Eun Sook Yoo、Jongki Hong、Jae Sue Choi、Hyung Sik Kim、Hae Young Chung、Jee H. Jung

  DOI：10.1016/j.bmc.2010.12.046

  日期：2011.2

  A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1 beta, IL-6, and TNF-alpha) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-gamma-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 similar to 2 mu M). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1 beta, IL-6, and TNF-alpha) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads. (C) 2010 Elsevier Ltd. All rights reserved.
• 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