5'-fluoro-2,3-dimethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxylic acid | 1033762-25-2

• 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: 5'-fluoro-2,3-dimethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxylic acid
• 英文别名: 6-Fluoro-4',5'-dimethylspiro[1,2-dihydroindene-3,12'-13-oxa-3,6-diazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7-tetraene]-8'-carboxylic acid
• CAS: 1033762-25-2
• 化学式: C₂₁H₁₉FN₂O₃
• 分子量: 366.392
• InChiKey: RQBJDRLKFOHGEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-fluoro-2,3-dimethyl-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38%的产率得到5'-fluoro-N,N,2,3-tetramethyl-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
• 作为产物：
  描述：

  ethyl 5'-fluoro-2,3-dimethyl-2',3',7,8-tetrahydrospiro-[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxylate 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以200 mg的产率得到5'-fluoro-2,3-dimethyl-2',3',7,8-tetrahydrospiro[imidazo[1,2-a]pyrano[2,3-c]pyridine-9,1'-indene]-6-carboxylic acid
  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

• [EN] PHARMACEUTICALLY ACTIVE SPIRO-SUBSTITUTED IMIDAZOPYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS D'IMIDAZOPYRIDINE SUBSTITUÉS PAR SPIRO, PHARMACEUTIQUEMENT ACTIFS
  申请人：NYCOMED GMBH

  公开号：WO2008071766A2

  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] L'invention concerne des composés représentés par la formule (1), dans laquelle les substituants et symboles sont tels que définis dans la description. Les composés inhibent la sécrétion de l'acide gastrique.
• 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.