octyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate | 1254178-12-5

• 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: octyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate
• CAS: 1254178-12-5
• 化学式: C₅₁H₅₆N₆O₃
• 分子量: 801.044
• InChiKey: IFFUPPAMPHLQSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.79
• 重原子数：
  60.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107.95
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  octyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以91%的产率得到octyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate
  参考文献：
  名称：

  Novel amides and esters prodrugs of olmesartan: Synthesis, bioconversion, and pharmacokinetic evaluation

  摘要：

  Synthesis of novel amides and esters prodrugs of olmesartan is described. Their in vitro stability in rat plasma was tested. The results showed that the ester derivative IIa with n-octyl substituted dioxolone moiety was rapidly converted into olmesartan within 30 min. The pharmacokinetic parameters of IIa were studied and compared with those of olmesartan medoxomil. Compound IIa is proposed to be a promising prodrug of olmesartan. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.07.089
• 作为产物：
  描述：

  4-(1-羟基-1-甲基乙基)-2-丙基-1H-咪唑-5-羧酸乙酯 在 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 N,N-二甲基乙酰胺 、 水 、 异丙醇 、 丙酮 为溶剂， 反应 16.5h， 生成 octyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(1-trityltetrazol-5-yl)phenyl]phenylmethyl}imidazole-5-carboxylate
  参考文献：
  名称：

  Design, synthesis, bioconversion, and pharmacokinetics evaluation of new ester prodrugs of olmesartan

  摘要：

  Synthesis of new ester prodrugs of olmesartan is described. Their in vitro stabilities in simulated gastric juice, rat plasma, and rat liver microsomes were tested. And the pharmacokinetic parameters for olmesartan after their oral administration were also estimated and compared with those in case of olmesartan medoxomil. Compounds 13 and 14 demonstrated high stability in simulated gastric juice and were rapidly metabolized to olmesartan in rat liver microsomes and rat plasma in vitro. In addition, C-max and AUC(last) parameters were significantly increased in case of compounds 13 and 14 compared with olmesartan medoxomil. These results indicate that compounds 13 and 14 with cyclohexylcarboxyethyl and adamantylcarboxymethyl promoieties, respectively, are promising prodrugs of olmesartan with markedly increased oral bioavailability. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.019