N,N,2,3,4'-pentamethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxamide | 1033762-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: N,N,2,3,4'-pentamethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxamide
• 英文别名: N,N,4',5',7-pentamethylspiro[1,2-dihydroindene-3,12'-13-oxa-3,6-diazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7-tetraene]-8'-carboxamide
• CAS: 1033762-29-6
• 化学式: C₂₄H₂₇N₃O₂
• 分子量: 389.497
• InChiKey: FNMFHHBMZSWLCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,4'-trimethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxylic acid 、 二甲胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到N,N,2,3,4'-pentamethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxamide
  参考文献：
  名称：

  Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) as inhibitors of gastric acid secretion

  摘要：

  Asymmetric and symmetric spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) were prepared using a synthetic approach that comprised a cross-metathesis reaction and an acid-catalyzed cycloisomerisation as key steps. The target compounds constitute potent inhibitors of the gastric proton pump enzyme with inhibitory activity comparable to potassium-competitive acid blockers (P-CABs) belonging to the known 9-aryl-7H-8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridine series. Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9,2'-indenes) represent the first example for P-CABs, in which the distance between the heterocyclic scaffold and the aryl residue has been modified, and are promising candidates for further development as anti-ulcer drugs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.055