4-(allyloxy)-N,N,1,2-dimethyl-1H-benzimidazol-6-carboxamide | 1034023-24-9

• 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: 4-(allyloxy)-N,N,1,2-dimethyl-1H-benzimidazol-6-carboxamide
• CAS: 1034023-24-9
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: ZDWRINNUSXZGMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(allyloxy)-N,N,1,2-dimethyl-1H-benzimidazol-6-carboxamide 反应 4.0h， 以81%的产率得到5-allyl-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of potential metabolites of the potassium-competitive acid blocker BYK405879

  摘要：

  Four potential metabolites of the potassium-competitive acid blocker BYK 405879 (1) were synthesized which might be formed in vivo by enzymatic oxidation of the pyran moiety or the methyl groups attached to the (hetero) aromatic system. In all cases, the oxidation of the parent compound 1 was accompanied by a significant loss of pharmacological activity and by a decrease in lipophilicity. The target compounds 6, 14, 20, and 21 constitute valuable tool substances for the investigation of the metabolic fate of BYK 405879 (1). (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.070
• 作为产物：
  描述：

  7-羟基-N,N,2,3-四甲基苯并咪唑-5-甲酰胺 、 3-溴丙烯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以78%的产率得到4-(allyloxy)-N,N,1,2-dimethyl-1H-benzimidazol-6-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of potential metabolites of the potassium-competitive acid blocker BYK405879

  摘要：

  Four potential metabolites of the potassium-competitive acid blocker BYK 405879 (1) were synthesized which might be formed in vivo by enzymatic oxidation of the pyran moiety or the methyl groups attached to the (hetero) aromatic system. In all cases, the oxidation of the parent compound 1 was accompanied by a significant loss of pharmacological activity and by a decrease in lipophilicity. The target compounds 6, 14, 20, and 21 constitute valuable tool substances for the investigation of the metabolic fate of BYK 405879 (1). (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.070

文献信息

• WO2008/71765
  申请人：——

  公开号：——

  公开（公告）日：——