2-(1-Benzyl-2-oxo-2-phenyl-ethyl)-5-butyl-4-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one | 149810-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(1-Benzyl-2-oxo-2-phenyl-ethyl)-5-butyl-4-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one
• CAS: 149810-25-3
• 化学式: C₅₄H₄₇N₇O₂
• 分子量: 826.013
• InChiKey: GPMTUAYUZZUIDL-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.26
• 重原子数：
  63.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  100.49
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(1-Benzyl-2-oxo-2-phenyl-ethyl)-5-butyl-4-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one 在 溶剂黄146 作用下， 以80%的产率得到2-(1-benzoyl-2-phenylethyl)-5-butyl-2,4-dihydro-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis and structure-activity relationships of nonpeptide, potent triazolone-based angiotensin II receptor antagonists

  摘要：

  2,5-Dibutyl-2,4-dihydro-4-[[2-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4'-yl]methyl] -3H-1,2,4-triazol-3-one, SC-51316, was synthesized as a potent and orally active angiotensin II (AII) receptor antagonist with a long duration of action. To explore the lipophilic pocket in the AII receptor interacting with the substituent at the 2-position of triazolone-based antagonists, a series of compounds were prepared and evaluated for receptor binding affinity and antagonism of AII-contracted rabbit aortic rings. It has been found that the pocket is very spacious and can accommodate different sizes of lipophilic groups and various functionalities. Acidic groups generally result in a slight decrease in binding affinity. Branched chains are unfavorable. The freedom of rotation around C2-C3 in the flexible side chain is crucial for good binding. The 2-phenylethyl-substituted triazolone analogue exhibits the highest in vitro potency among all compounds that have been synthesized.

  DOI：

  10.1021/jm00067a015
• 作为产物：
  描述：

  5-n-butyl-2,4-dihydro-4-<<2'-(N-trityltetrazol-5-yl)biphenyl-4-yl>methyl>-3H-1,2,4-triazol-3-one 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 2-(1-Benzyl-2-oxo-2-phenyl-ethyl)-5-butyl-4-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  Synthesis and structure-activity relationships of nonpeptide, potent triazolone-based angiotensin II receptor antagonists

  摘要：

  2,5-Dibutyl-2,4-dihydro-4-[[2-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4'-yl]methyl] -3H-1,2,4-triazol-3-one, SC-51316, was synthesized as a potent and orally active angiotensin II (AII) receptor antagonist with a long duration of action. To explore the lipophilic pocket in the AII receptor interacting with the substituent at the 2-position of triazolone-based antagonists, a series of compounds were prepared and evaluated for receptor binding affinity and antagonism of AII-contracted rabbit aortic rings. It has been found that the pocket is very spacious and can accommodate different sizes of lipophilic groups and various functionalities. Acidic groups generally result in a slight decrease in binding affinity. Branched chains are unfavorable. The freedom of rotation around C2-C3 in the flexible side chain is crucial for good binding. The 2-phenylethyl-substituted triazolone analogue exhibits the highest in vitro potency among all compounds that have been synthesized.

  DOI：

  10.1021/jm00067a015