N-Arachidonyltyramine | 162660-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-Arachidonyltyramine
• 英文别名: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenethyl)icosa-5,8,11,14-tetraenamide；arachidonoyl tyramine；N-arachidonoyl-tyramine；(5Z,8Z,11Z,14Z)-N-[2-(4-hydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
• CAS: 162660-90-4
• 化学式: C₂₈H₄₁NO₂
• 分子量: 423.639
• InChiKey: OJXVMIIWGTVRRX-DOFZRALJSA-N

物化性质

• 沸点：
  603.2±55.0 °C(predicted)
• 密度：
  0.982±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Arachidonyltyramine 、 [11C]methyl iodide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 [11C]-4-Methoxyphenethylarachidonoylamide
  参考文献：
  名称：

  Synthesis, In Vitro and In Vivo Evaluation, and Radiolabeling of Aryl Anandamide Analogues as Candidate Radioligands for In Vivo Imaging of Fatty Acid Amide Hydrolase in the Brain

  摘要：

  Fatty acid amide hydrolyase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids in the brain. Imaging FAAH in vivo using PET or SPECT is important to deeper understanding of its role in neuropsychiatric disorders. However, at present, no radioligand is available for mapping the enzyme in vivo. Here, we synthesized 18 aryl analogues of anandamide, FAAH's endogenous substrate, and in vitro evaluated their potential as metabolic trapping tracers. Interaction studies with recombinant FAAH revealed good to very good interaction of the methoxy substituted aryl anandamide analogues 17, 18, 19, and 20 with FAAH and they were identified as competing substrates, Compounds 17 and 18 did not display significant binding to CB1 and CB2 cannabinoid receptors and stand out as potential candidate metabolic trapping tracers. They were successfully labeled with C-11 in good yields and high radiochemical purity and displayed brain uptake in C57BL/6J mice. Radioligands [C-11]-17 and [C-11]-18 merit further investigation in vivo.

  DOI：

  10.1021/jm900324e
• 作为产物：
  描述：

  对羟基苯乙胺 、 花生四烯酸 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到N-Arachidonyltyramine
  参考文献：
  名称：

  Synthesis, In Vitro and In Vivo Evaluation, and Radiolabeling of Aryl Anandamide Analogues as Candidate Radioligands for In Vivo Imaging of Fatty Acid Amide Hydrolase in the Brain

  摘要：

  Fatty acid amide hydrolyase (FAAH) is one of the main enzymes responsible for terminating the signaling of endocannabinoids in the brain. Imaging FAAH in vivo using PET or SPECT is important to deeper understanding of its role in neuropsychiatric disorders. However, at present, no radioligand is available for mapping the enzyme in vivo. Here, we synthesized 18 aryl analogues of anandamide, FAAH's endogenous substrate, and in vitro evaluated their potential as metabolic trapping tracers. Interaction studies with recombinant FAAH revealed good to very good interaction of the methoxy substituted aryl anandamide analogues 17, 18, 19, and 20 with FAAH and they were identified as competing substrates, Compounds 17 and 18 did not display significant binding to CB1 and CB2 cannabinoid receptors and stand out as potential candidate metabolic trapping tracers. They were successfully labeled with C-11 in good yields and high radiochemical purity and displayed brain uptake in C57BL/6J mice. Radioligands [C-11]-17 and [C-11]-18 merit further investigation in vivo.

  DOI：

  10.1021/jm900324e

文献信息

• Congeners of acetaminophen and related compounds as substrates for fatty acid conjugation and their use in treatment of pain, fever and inflammation
  申请人：——

  公开号：US20040209959A1

  公开（公告）日：2004-10-21

  The present invention relates to new analgesic, antipyretic and/or anti-inflammatory compounds represented by the general formula X—Y, in which X is a benzyl group, a saturated or unsaturated cycloalkyl group (I,II) or a non-cyclic, straight or branched alkyl group (III,IV).

  本发明涉及通式 X-Y 所代表的新型镇痛、解热和/或消炎化合物，其中 X 是苄基、饱和或不饱和环烷基（I,II）或非环状、直链或支链烷基（III,IV）。
• Termitomycamides A to E, Fatty Acid Amides Isolated from the Mushroom <i>Termitomyces titanicus</i>, Suppress Endoplasmic Reticulum Stress
  作者：Jae-Hoon Choi、Kohei Maeda、Kaoru Nagai、Etsuko Harada、Mitsuo Kawade、Hirofumi Hirai、Hirokazu Kawagishi

  DOI：10.1021/ol102186p

  日期：2010.11.5

  Five fatty acid amides, termitomycamides A to E (1 to 5), were isolated from the giant edible mushroom Termitomyces titanicus. The structures of 1-5 were determined by the interpretation of spectral data and/or synthesis. Compounds 2 and 5 showed protective activity against endoplasmic reticulum stress-dependent cell death.
• COMPOSITIONS AND METHODS FOR INHIBITING AN ISOFORM OF HUMAN MANGANESE SUPEROXIDE DISMUTASE
  申请人：Mito Tek, LLC

  公开号：EP1636335B1

  公开（公告）日：2012-07-11
• [EN] CONGENERS OF ACETAMINOPHEN AND RELATED COMPOUNDS AS SUBSTRATES FOR FATTY ACID CONJUGATION AND THEIR USE IN TREATMENT OF PAIN, FEVER AND INFLAMMATION<br/>[FR] SUBSTANCES ORGANOLEPTIQUES D'ACETAMINOPHENE ET COMPOSES ASSOCIES UTILISES COMME SUBSTRATS POUR CONJUGAISON D'ACIDES GRAS ET UTILISATION DE CES SUBSTANCES DANS LE TRAITEMENT DE LA DOULEUR, DE LA FIEVRE ET DES INFLAMMATIONS
  申请人：HOEGESTAETT EDWARD

  公开号：WO2003007875A2

  公开（公告）日：2003-01-30

  The present invention relates to new analgesic, antipyretic and/or anti-inflammatory compounds represented by the general formula X - Y, in which X is a benzyl group, a saturated or unsaturated cycloalkyl group (I,II) or a non-cyclic, straight or branched alkyl group (III,IV).
• [EN] FATTY ACID CONJUGATION AS A METHOD FOR SCREENING OF POTENTIALLY BIOACTIVE SUBSTANCES<br/>[FR] CONJUGAISON D'ACIDES GRAS EN TANT QUE METHODE DE CRIBLAGE DE SUBSTANCES POTENTIELLEMENT BIOACTIVES
  申请人：HOEGESTAETT EDWARD

  公开号：WO2003008632A1

  公开（公告）日：2003-01-30

  The present invention relates to a method for screening of compounds or molecules that undergo conjugation with fatty acids present in a mammal body, including humans, whereby a compound to be tested is brought into contact with a fatty acid together with a tissue homogenate or an enzyme, whereupon any conjugation between the compound and any fatty acid present in said homogenate is determined with regard to presence of fatty acid amides, esters or thioesters, as well as a kit for conjugation of such compounds or molecules with fatty acids.