5-Methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carbonitrile | 120905-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-Methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carbonitrile
• CAS: 120905-68-2
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: ACZAQBSYVHNGJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carbonitrile 在 三正丁基叠氮化锡 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 87.0h， 以38%的产率得到5-Methoxy-3-(1-methylethoxy)-1-phenyl-2-(1H-tetrazol-5-yl)-1H-indole
  参考文献：
  名称：

  Novel indolecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic potential of a series of novel indolecarboxamidotetrazoles are described. A number of compounds inhibit the release of histamine from anti-IgE-stimulated basophilic leukocytes obtained from allergic donors. Optimal inhibition is exhibited by compounds with 3-alkoxy, 5-methoxy, and 1-phenyl substituents on the indole core structure. Compound 8d (5-methoxy-3-(1-methylethoxy)-1-phenyl-N-1H-tetrazol-5-yl-1H -indole-2-carboxamide; designated CI-949) is a potent inhibitor of histamine release from human basophils and from guinea pig and human chopped lung.

  DOI：

  10.1021/jm00126a036
• 作为产物：
  描述：

  2-[(Cyanomethyl)phenylamino]-5-methoxy-benzoic acid 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 69.0h， 生成 5-Methoxy-3-(1-methylethoxy)-1-phenyl-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Novel indolecarboxamidotetrazoles as potential antiallergy agents

  摘要：

  The synthesis and antiallergic potential of a series of novel indolecarboxamidotetrazoles are described. A number of compounds inhibit the release of histamine from anti-IgE-stimulated basophilic leukocytes obtained from allergic donors. Optimal inhibition is exhibited by compounds with 3-alkoxy, 5-methoxy, and 1-phenyl substituents on the indole core structure. Compound 8d (5-methoxy-3-(1-methylethoxy)-1-phenyl-N-1H-tetrazol-5-yl-1H -indole-2-carboxamide; designated CI-949) is a potent inhibitor of histamine release from human basophils and from guinea pig and human chopped lung.

  DOI：

  10.1021/jm00126a036