ethyl 3-butyl-4,5-dihydro-5-oxo-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-1,2,4-triazole-1-hexanoate | 149810-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-butyl-4,5-dihydro-5-oxo-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-1,2,4-triazole-1-hexanoate
• 英文别名: ethyl 6-[3-butyl-5-oxo-4-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-1,2,4-triazol-1-yl]hexanoate
• CAS: 149810-27-5
• 化学式: C₂₈H₃₅N₇O₃
• 分子量: 517.631
• InChiKey: PJQHMCYBMZPKDR-UHFFFAOYSA-N

物化性质

• 沸点：
  679.0±65.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-butyl-4,5-dihydro-5-oxo-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-1,2,4-triazole-1-hexanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-butyl-4,5-dihydro-5-oxo-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-1,2,4-triazole-1-hexanoic acid
  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 ethyl 3-butyl-4,5-dihydro-5-oxo-4-<<2'-(1H-tetrazol-5-yl)<1,1'-biphenyl>-4-yl>methyl>-1H-1,2,4-triazole-1-hexanoate
  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

文献信息

• Synthesis and structure-activity relationships of nonpeptide, potent triazolone-based angiotensin II receptor antagonists
  作者：Horng Chih Huang、David B. Reitz、Timothy S. Chamberlain、Gillian M. Olins、Valerie M. Corpus、Ellen G. McMahon、Maria A. Palomo、John P. Koepke、Glenn J. Smits

  DOI：10.1021/jm00067a015

  日期：1993.7

  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.