(9Z,12Z)-N-[2-(3,4-二羟基苯基)乙基]十八碳-9,12-二烯酰胺 | 105955-12-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (9Z,12Z)-N-[2-(3,4-二羟基苯基)乙基]十八碳-9,12-二烯酰胺
• 中文别名: N-亚油酰多巴胺
• 英文名称: (Z,Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]-octadeca-9,12-dienamide
• 英文别名: (9Z,12Z)-N-(3,4-dihydroxyphenethyl)octadeca-9,12-dienamide；N-linoleoyl dopamine；N-linoleoyldopamine；(9Z,12Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]octadeca-9,12-dienamide
• CAS: 105955-12-2
• 化学式: C₂₆H₄₁NO₃
• 分子量: 415.616
• InChiKey: SZYHQIGUKQSEJD-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 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：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (9Z,12Z)-N-[2-(3,4-二羟基苯基)乙基]十八碳-9,12-二烯酰胺
  参考文献：
  名称：

  Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.

  摘要：

  N-反式和N-顺式-阿魏酰基酪胺是从印尼药用植物空心菜（旋花科）中分离得到的体外前列腺素（PG）合成抑制剂。为了阐明结构活性关系，合成了可能由天然存在的肉桂酸和β-苯乙胺组合得到的肉桂酰-β-苯乙胺，并测试了它们对PG合成酶和花生四烯酸5-脂氧合酶的抑制活性。含有儿茶酚基团的化合物，如N-咖啡酰基-β-苯乙胺（CaP），显示出对PG合成酶更高的抑制效果。儿茶酚基团被发现对抑制花生四烯酸5-脂氧合酶至关重要。对浓度依赖性PG生物合成效应的研究表明，CaP在较低浓度范围内增强了PG生物合成，而在较高浓度下抑制了反应。通过纯化的PG内过氧化物合成酶和微粒体PG合成酶研究了CaP对每个反应步骤的影响。CaP抑制了环氧合酶反应，同时增强了氢过氧化物酶反应。从多巴胺和脂肪酸合成了含有儿茶酚和脂溶性基团的N-酰基多巴胺，以测试它们对花生四烯酸5-脂氧合酶的抑制效果。N-亚油酰多巴胺是最活跃的化合物，在我们的测定系统中其IC50值为2.3nM，而作为5-脂氧合酶特异性抑制剂的AA 861的IC50值为8nM。

  DOI：

  10.1248/cpb.40.396

文献信息

• A Convenient Protocol for the Synthesis of Fatty Acid Amides
  作者：Jens Nolsøe、Silje Johansson、Tonje Johannessen、Christiane Ellefsen、Mali Ristun、Simen Antonsen、Trond Hansen、Yngve Stenstrøm

  DOI：10.1055/s-0037-1611939

  日期：2019.1

  Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical,

  已经从哺乳动物和植物来源报道了几类生物存在的脂肪酸酰胺。许多与哺乳动物来源的脂肪酸结合的酰胺表现出对个体受体的特异性激活。它们作为药理学工具或作为开发新疗法的先导化合物的潜力引起了人们极大的兴趣。因此，需要在不影响敏感功能的几何形状或位置的情况下，通过实用、高产和可扩展的协议来获取此类酰胺。满足所有这些要求的方案包括用羰基二咪唑 (CDI) 活化相应的酸，然后与所需的胺或其盐酸盐反应。已经以通常高产率制备了五十多种化合物。
• PHARMACEUTICAL AGENT FOR PREVENTION AND TREATMENT OF SKIN DISEASE INDUCED BY ACCELERATED KERATINIZATION
  申请人：Kyoto University

  公开号：EP2127673A1

  公开（公告）日：2009-12-02

  A medicament for prophylactic and/or therapeutic treatment of a dermatosis resulting from excessively advanced keratinization, such as non-hereditary inflammatory keratosis and hereditary congenital keratosis, which comprises a substance selected from the group consisting of a cannabinoid agonist and a vanilloid agonist as an active ingredient.

  一种用于预防和/或治疗过度角化引起的皮肤病（如非遗传性炎症性角化病和遗传性先天性角化病）的药物，其活性成分包括一种从大麻素激动剂和香草素激动剂组成的组中选出的物质。
• 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.
• HIGHLY EFFICIENT SYNTHESIS OF FATTY ACID DOPAMIDES
  作者：Z. Czarnocki、M. P. Matuszewska、I. Matuszewska

  DOI：10.1080/00304949809355327

  日期：1998.12
• MIKAVA, USIO
  作者：MIKAVA, USIO

  DOI：——

  日期：——