N,N,2,3-tetramethyl-1',3',7,8-tetrahydrospiro[imidazo-[1,2-a]pyrano[2,3-c]pyridine-9,2'-indene]-6-carboxamide | 1033762-30-9

• 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-tetramethyl-1',3',7,8-tetrahydrospiro[imidazo-[1,2-a]pyrano[2,3-c]pyridine-9,2'-indene]-6-carboxamide
• 英文别名: N,N,4',5'-tetramethylspiro[1,3-dihydroindene-2,12'-13-oxa-3,6-diazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7-tetraene]-8'-carboxamide
• CAS: 1033762-30-9
• 化学式: C₂₃H₂₅N₃O₂
• 分子量: 375.47
• InChiKey: UWPMKRFLLUSEIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  7-[2-(1,3-dihydro-2H-inden-2-ylidene)ethyl]-8-hydroxy-n,n,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide 在 三氟化硼乙醚 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 16.0h， 以39%的产率得到N,N,2,3-tetramethyl-1',3',7,8-tetrahydrospiro[imidazo-[1,2-a]pyrano[2,3-c]pyridine-9,2'-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

文献信息

• Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) as inhibitors of gastric acid secretion
  作者：Andreas Marc Palmer、Sandra Chrismann、Gabriela Münch、Christof Brehm、Peter Jan Zimmermann、Wilm Buhr、Jörg Senn-Bilfinger、Martin Philipp Feth、Wolfgang Alexander Simon

  DOI：10.1016/j.bmc.2008.10.055

  日期：2009.1

  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.