termitomycamide E | 1177258-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: termitomycamide E
• 英文别名: (9Z,12Z)-N-[2-(4-hydroxyphenyl)ethyl]octadeca-9,12-dienamide
• CAS: 1177258-62-6
• 化学式: C₂₆H₄₁NO₂
• 分子量: 399.617
• InChiKey: JTSNNDBVDQFVEG-HZJYTTRNSA-N

物化性质

• 溶解度：
  DMF：30 mg/ml； DMSO：30 mg/ml；乙醇：30 mg/ml；乙醇:PBS (pH7.2)(1:20): 0.05 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  29
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 termitomycamide E 在 四丁基氢氧化铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 [11C]-4-Methoxyphenethyllinoleoylamide
  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 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以77%的产率得到termitomycamide E
  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

• 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.
• 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
  作者：Leonie wyffels、Giulio G. Muccioli、Sylvie De Bruyne、Lieselotte Moerman、Johan Sambre、Didier M. Lambert、Filip De Vos

  DOI：10.1021/jm900324e

  日期：2009.8.13

  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.