17-Hydroxy-heptadeca-5,8,11,14-tetraynoic acid methyl ester | 903514-42-1

• 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: 17-Hydroxy-heptadeca-5,8,11,14-tetraynoic acid methyl ester
• 英文别名: Methyl 17-hydroxyheptadeca-5,8,11,14-tetraynoate
• CAS: 903514-42-1
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: PPOYYYOHFLSWRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-Hydroxy-heptadeca-5,8,11,14-tetraynoic acid methyl ester 在 P-2 Ni 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (5Z,8Z,11Z,14Z)-17-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-heptadeca-5,8,11,14-tetraenoic acid methyl ester
  参考文献：
  名称：

  潜在的可光活化的芳酰胺类似物的合成。

  摘要：

  通过跳过的四炔中间体的选择性加氢合成了潜在的光催化的金刚烷酰胺类似物。该化合物可能是寻找新的大麻素受体的有用工具。

  DOI：

  10.1016/j.bmcl.2006.04.059
• 作为产物：
  描述：

  5-己炔酸甲酯 在 copper(l) iodide 、 四溴化碳 、 potassium carbonate 、 caesium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 17-Hydroxy-heptadeca-5,8,11,14-tetraynoic acid methyl ester
  参考文献：
  名称：

  潜在的可光活化的芳酰胺类似物的合成。

  摘要：

  通过跳过的四炔中间体的选择性加氢合成了潜在的光催化的金刚烷酰胺类似物。该化合物可能是寻找新的大麻素受体的有用工具。

  DOI：

  10.1016/j.bmcl.2006.04.059

文献信息

• Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity
  作者：Laurence Balas、Thierry Durand、Sattyabrata Saha、Inneke Johnson、Somnath Mukhopadhyay

  DOI：10.1021/jm8011382

  日期：2009.2.26

  Endocannabinoids are endogenous polyunsaturated fatty acids involved in a multitude of health and disease processes. Recently, several lines of evidence suggest the presence of a novel non-CB1/CB2 anandamide receptor in endothelial cells. Thus, we synthesized two types of photoaffinity probes that contain either an arylazide group or a diazirin moiety, together with a fluorescent analogue. The key steps rely on selective hydrogenation of skipped tetrayne backbones and on copper-mediated cross-coupling reactions between diynic precursors. Three synthetic routes were investigated. In biological functional assays, we found that both the arylazide and the fluorescent probes induced robust increases in matrix metalloprotease activity and produced positive angiogenic responses in in vitro endothelial cell tube formation assays. Irradiation of the arylazide probe nicely enhanced this effect in both HUVEC and CBI-KO HUVEC. These results suggest that the arylazide and the fluorescent probes can be used to identify "non-C131/CB2 anandamide receptor" from endothelial cells.
• Cannabinergic Lipid Ligands
  申请人：Makriyannis Alexandros

  公开号：US20090163557A1

  公开（公告）日：2009-06-25

  One aspect of this disclosure relates generally to lipid compounds that exert diverse effects in the endocannabinoid system, such as regulating CB1 and CB2 receptor or moderating other bio-macromolecules within the endocannabinoid system. Some of the compounds showed improved receptor binding affinity, and/or improved receptor subtype selectivity, and improved bio-stability. Some of the compounds exhibit activities to regulate the enzymes that moderate the bio-disposal of endogenous cannabinoids, such as the fatty acid amide hydrolase (FAAH). Some of the compounds exhibit activities to inhibit the anandamide transporter. Other aspects of the invention are pharmaceutical preparations employing these ligands and methods of administering therapeutically effective amounts of the preparations to provide a physiological effect.
• US8202893B2
  申请人：——

  公开号：US8202893B2

  公开（公告）日：2012-06-19
• Synthesis of a potential photoactivatable anandamide analog
  作者：Laurence Balas、Maria Grazia Cascio、Vincenzo Di Marzo、Thierry Durand

  DOI：10.1016/j.bmcl.2006.04.059

  日期：2006.7

  A potential photoreactive analog of anandamide was synthesized via selective hydrogenation of a skipped tetrayne intermediate. This compound might be a useful tool to search for new cannabinoid receptors.

  通过跳过的四炔中间体的选择性加氢合成了潜在的光催化的金刚烷酰胺类似物。该化合物可能是寻找新的大麻素受体的有用工具。