5-butyl-2,4-dihydro-2-<2-(2,5-dimethoxyphenyl)-2-oxo-ethyl>-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-3H-1,2,4-triazol-3-one | 139476-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-butyl-2,4-dihydro-2-<2-(2,5-dimethoxyphenyl)-2-oxo-ethyl>-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-3H-1,2,4-triazol-3-one
• 英文别名: 5-butyl-2-[2-(2,5-dimethoxyphenyl)-2-oxoethyl]-4-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-1,2,4-triazol-3-one
• CAS: 139476-34-9
• 化学式: C₃₀H₃₁N₇O₄
• 分子量: 553.621
• InChiKey: YFIVSTVKNZPDDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-butyl-2,4-dihydro-2-<2-(2,5-dimethoxyphenyl)-2-oxo-ethyl>-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-3H-1,2,4-triazol-3-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 5-butyl-2,4-dihydro-2-<2-(2,5-dimethoxyphenyl)-2-hydroxyethyl>-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：

  厄贝沙坦杂质19 在 palladium on activated charcoal 吡啶 、 trimethyltin azide 、 potassium tert-butylate 、 氢气 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 212.0h， 生成 5-butyl-2,4-dihydro-2-<2-(2,5-dimethoxyphenyl)-2-oxo-ethyl>-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