N-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]hex-5-ynamide | 1118097-42-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]hex-5-ynamide
• CAS: 1118097-42-9
• 化学式: C₂₅H₃₃NO₂Si
• 分子量: 407.628
• InChiKey: POEGBTHZNXOYLD-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 N-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]hex-5-ynamide 在 乙基溴化镁 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以27%的产率得到(Z)-N,N'-bis[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]hexadec-8-en-5,11-diynediamide
  参考文献：
  名称：

  Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity

  摘要：

  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.

  DOI：

  10.1021/jm8011382
• 作为产物：
  描述：

  (2R)-1-{[tert-butyl(diphenyl)silyl]oxy}propan-2-amine 、 5-己炔酸 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到N-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]hex-5-ynamide
  参考文献：
  名称：

  Total Synthesis of Photoactivatable or Fluorescent Anandamide Probes: Novel Bioactive Compounds with Angiogenic Activity

  摘要：

  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.

  DOI：

  10.1021/jm8011382

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.