(9Z,12Z)-N-isopropyloctadeca-9,12-dienamide | 3140-45-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (9Z,12Z)-N-isopropyloctadeca-9,12-dienamide
• 英文别名: N-(1-methylethyl)-(9Z,12Z)octadecadienamide；(Z,Z)-N-isopropyl-octadeca-9,12-dienamide；N-isopropyllinoleoylamide；N-Isopropyllinolamid；Linoleamide, N-isopropyl-；(9Z,12Z)-N-propan-2-yloctadeca-9,12-dienamide
• CAS: 3140-45-2
• 化学式: C₂₁H₃₉NO
• 分子量: 321.547
• InChiKey: GHLUXRXWPBHFNB-MURFETPASA-N

物化性质

• 沸点：
  160-167 °C(Press: 0.02 Torr)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 异丙胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 13.0h， 生成 (9Z,12Z)-N-isopropyloctadeca-9,12-dienamide
  参考文献：
  名称：

  Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.12.046

文献信息

• Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development
  作者：Lionel Faure、Ronaldo Cavazos、Bibi Rafeiza Khan、Robby A. Petros、Peter Koulen、Elison B. Blancaflor、Kent D. Chapman

  DOI：10.1016/j.phytochem.2014.11.011

  日期：2015.2

  hydrolase (FAAH) has been described as a key contributor to NAE hydrolysis; however, no enzyme has been associated with alkamide degradation in plants. Herein reported is synthesis of 12 compounds structurally similar to a naturally occurring alkamide (N-isobutyl-(2E,6Z,8E)decatrienamide or affinin) with different acyl compositions more similar to plant NAEs and various amino alkyl head groups. These "hybrid"

  烷酰胺和 N-酰基乙醇胺 (NAE) 是影响植物发育的生物活性、酰胺连接的脂质。烷基酰胺仅限于高等植物的几个科和一些真菌，而 NAE 是植物和动物中广泛存在的信号分子。脂肪酸酰胺水解酶 (FAAH) 已被描述为 NAE 水解的关键因素；然而，没有酶与植物中的烷酰胺降解有关。本文报道了 12 种结构类似于天然存在的烷酰胺（N-异丁基-（2E，6Z，8E）十碳三烯酰胺或亲和素）的化合物的合成，具有不同的酰基组成，更类似于植物 NAE 和各种氨基烷基头基。测试了这些“混合”合成烷酰胺对重组拟南芥 FAAH 的活性及其对植物发育的影响（即，子叶扩张和初生根长度）。在一些合成的烷酰胺（如 N-乙基月桂酰胺）存在下，在体外发现 FAAH 对 NAE 的活性显着增加 (4)。发现这种“增强”效应至少部分是由于乙醇胺对 FAAH 产物抑制的缓解，而不是由于 FAAH 酶的寡聚化状态的改变。对于这些醇酰胺中的一些，观察到幼苗生长的抑制，FAAH
• COMPLEX OF NUCLEIC ACID MEDICINE AND MULTIBRANCHED LIPID
  申请人：SHIONOGI & CO., LTD.

  公开号：US20200384010A1

  公开（公告）日：2020-12-10

  The purpose of the present invention is to provide novel complexes that improve the effect of nucleic acid medicines. Provided is a complex in which a multibranched lipid(s) binds through a linker to a strand of an oligonucleotide comprising a nucleic acid medicine having suppressing activity of the target gene expression.
• 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.