(8S)-8-[2-(hydroxymethyl)phenyl]-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxamide | 917960-16-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (8S)-8-[2-(hydroxymethyl)phenyl]-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxamide
• CAS: 917960-16-8
• 化学式: C₂₂H₂₅N₃O₃
• 分子量: 379.459
• InChiKey: NXZXNXAFLREDIU-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8S)-8-[2-(hydroxymethyl)phenyl]-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxamide 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 生成 (8S)-8-(2-formylphenyl)-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-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：

  (8S)-8-(2-benzyloxymethyl-phenyl)-2,3-dimethyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid dimethylamide 在 磷酸 作用下， 反应 1.0h， 以36%的产率得到(8S)-8-[2-(hydroxymethyl)phenyl]-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-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