etonitazenediazonium | 118409-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: etonitazenediazonium
• 英文别名: 1-(2-Diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazole-5-diazonium；1-[2-(diethylamino)ethyl]-2-[(4-ethoxyphenyl)methyl]benzimidazole-5-diazonium
• CAS: 118409-77-1
• 化学式: C₂₂H₂₈N₅O
• 分子量: 378.497
• InChiKey: MSXQHUDFYMEGJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  etonitazenediazonium 在 sodium azide 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.5h， 生成 azidoetonitazene
  参考文献：
  名称：

  Photoactivatable opiate derivatives as irreversible probes of the .mu.-opioid receptor

  摘要：

  The synthesis of aryldiazonium and arylazido derivatives of carfentanil, etonitazene, and naltrexone and of a triazaspirodecane derivative is described. The chemical stability and the spectral characteristics of these compounds were verified, and their binding affinity constants for the different opioid receptor classes were determined, in the absence of light, from competition experiments. With the exception of the naltrexyl derivatives, which remained nonselective, all compounds tested displayed a pronounced mu-binding selectivity with mu/delta and mu/kappa ratios ranging from 12 to 1000. After irradiation, only the arylazido probes led to an irreversible mu-binding-site inactivation. This inactivation fulfilled the criteria for photoaffinity labeling such as protection against inactivation by other opiate ligands and absence of an effect of scavengers on the extent of the inactivation. Most of the photoactivatable probes formed long-lasting reversible complexes with the opioid binding sites: an efficient dissociation procedure was thus required to discriminate between pseudoirreversible and covalent complexes. The marked differences in labeling efficacy between aryldiazonium salts and their corresponding arylazido derivatives are discussed.

  DOI：

  10.1021/jm00171a020
• 作为产物：
  描述：

  1-[2-(diethylamino)ethyl]-2-(4-ethoxybenzyl)-1H-benzo[d]imidazol-5-amine 在 盐酸 、 三氟乙酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 etonitazenediazonium
  参考文献：
  名称：

  Photoactivatable opiate derivatives as irreversible probes of the .mu.-opioid receptor

  摘要：

  The synthesis of aryldiazonium and arylazido derivatives of carfentanil, etonitazene, and naltrexone and of a triazaspirodecane derivative is described. The chemical stability and the spectral characteristics of these compounds were verified, and their binding affinity constants for the different opioid receptor classes were determined, in the absence of light, from competition experiments. With the exception of the naltrexyl derivatives, which remained nonselective, all compounds tested displayed a pronounced mu-binding selectivity with mu/delta and mu/kappa ratios ranging from 12 to 1000. After irradiation, only the arylazido probes led to an irreversible mu-binding-site inactivation. This inactivation fulfilled the criteria for photoaffinity labeling such as protection against inactivation by other opiate ligands and absence of an effect of scavengers on the extent of the inactivation. Most of the photoactivatable probes formed long-lasting reversible complexes with the opioid binding sites: an efficient dissociation procedure was thus required to discriminate between pseudoirreversible and covalent complexes. The marked differences in labeling efficacy between aryldiazonium salts and their corresponding arylazido derivatives are discussed.

  DOI：

  10.1021/jm00171a020

文献信息

• Photoactivatable opiate derivatives as irreversible probes of the .mu.-opioid receptor
  作者：Jean Luc Galzi、Annick Mejean、Brigitte Ilien、Catherine Mollereau、Jean Claude Meunier、Maurice Goeldner、Christian Hirth

  DOI：10.1021/jm00171a020

  日期：1990.9

  The synthesis of aryldiazonium and arylazido derivatives of carfentanil, etonitazene, and naltrexone and of a triazaspirodecane derivative is described. The chemical stability and the spectral characteristics of these compounds were verified, and their binding affinity constants for the different opioid receptor classes were determined, in the absence of light, from competition experiments. With the exception of the naltrexyl derivatives, which remained nonselective, all compounds tested displayed a pronounced mu-binding selectivity with mu/delta and mu/kappa ratios ranging from 12 to 1000. After irradiation, only the arylazido probes led to an irreversible mu-binding-site inactivation. This inactivation fulfilled the criteria for photoaffinity labeling such as protection against inactivation by other opiate ligands and absence of an effect of scavengers on the extent of the inactivation. Most of the photoactivatable probes formed long-lasting reversible complexes with the opioid binding sites: an efficient dissociation procedure was thus required to discriminate between pseudoirreversible and covalent complexes. The marked differences in labeling efficacy between aryldiazonium salts and their corresponding arylazido derivatives are discussed.