5-allyl-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide | 1034023-26-1

• 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: 5-allyl-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide
• 英文别名: 7-hydroxy-N,N,2,3-tetramethyl-6-prop-2-enylbenzimidazole-5-carboxamide
• CAS: 1034023-26-1
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: JDWYMRBSCKDDSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-allyl-4-hydroxy-N,N,1,2-tetramethyl-1H-benzimidazole-6-carboxamide 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以100%的产率得到
  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：

  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

文献信息

• [EN] PHARMACEUTICALLY ACTIVE SPIRO-SUBSTITUTED BENZIMIDAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE SPIRO-SUBSTITUÉ ACTIFS D'UN POINT DE VUE PHARMACEUTIQUE
  申请人：NYCOMED GMBH

  公开号：WO2008071765A1

  公开（公告）日：2008-06-19

  [EN] The invention provides compounds of the formula (1), in which the substituents and symbols are as defined in the description. The compounds inhibit the secretion of gastric acid.
  [FR] Cette invention concerne des composés de formule (1), dans laquelle les substituants et les symboles sont tels que définis dans la description. Les composés inhibent la sécrétion d'acide gastrique.