5H-chromeno[2,3-c]pyridin | 38674-06-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5H-chromeno[2,3-c]pyridin
• 英文别名: 2-azaxanthene；3-azaxanthene；5H-chromeno[2,3-c]pyridine
• CAS: 38674-06-5
• 化学式: C₁₂H₉NO
• mdl: MFCD18450555
• 分子量: 183.21
• InChiKey: IYFHLNFKUVWJHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5H-chromeno[2,3-c]pyridin 、 过氧乙酸 以10%的产率得到
  参考文献：
  名称：

  PAVIA, MICHAEL R.;TAYLOR, CHARLES P.;HERSHENSON, FRED M.;LOBBESTAEL, SAND+, J. MED. CHEM., 31,(1988) N 4, 841-847

  摘要：

  DOI：
• 作为产物：
  描述：

  5H-chromeno[2,3-c]pyridin-5-one 在 汞 、 锌 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到5H-chromeno[2,3-c]pyridin
  参考文献：
  名称：

  3-Phenoxypyridine 1-oxides as anticonvulsant agents

  摘要：

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.

  DOI：

  10.1021/jm00399a027

文献信息

• [EN] AMINO-OXAZINES AND AMINO-DIHYDROTHIAZINE COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE<br/>[FR] COMPOSÉS D'AMINO-OXAZINES ET D'AMINO-DIHYDROTHIAZINE COMME MODULATEURS DE SÉCRÉTASE BÊTA ET PROCÉDÉS D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2013044092A1

  公开（公告）日：2013-03-28

  The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer's disease (AD) and related conditions. In one embodiment, the compounds have a general Formula I wherein A1, A2, A3, A4, A5, A6, L, R2, R7, X, Y and Z of Formula I are defined herein. The invention also includes use of these compounds in pharmaceutical compositions for treatment, prophylactic or therapeutic, of disorders and conditions related to the activity of beta-secretase protein. Such disorders include, for example, Alzheimer's Disease, cognitive deficits, cognitive impairment, schizophrenia and other central nervous system conditions related to and/or caused by the formation and/or deposition of plaque on the brain. The invention also comprises further embodiments of Formula I, intermediates and processes useful for the preparation of compounds of Formula I.

  本发明涉及一类新的化合物，用于调节β-分泌酶酶活性，并用于治疗β-分泌酶介导的疾病，包括阿尔茨海默病（AD）及相关病症。在一个实施例中，这些化合物具有一般的化学式I，其中化学式I中的A1、A2、A3、A4、A5、A6、L、R2、R7、X、Y和Z在此处定义。该发明还包括将这些化合物用于制备用于治疗与β-分泌酶蛋白活性相关的疾病和病症的药物组合物，包括例如阿尔茨海默病、认知缺陷、认知障碍、精神分裂症以及与大脑斑块的形成和/或沉积相关的其他中枢神经系统病症。该发明还涉及化学式I的进一步实施例、中间体和用于制备化合物的有用过程。
• PAVIA, MICHAEL R.;TAYLOR, CHARLES P.;HERSHENSON, FRED M.;LOBBESTAEL, SAND+, J. MED. CHEM., 31,(1988) N 4, 841-847
  作者：PAVIA, MICHAEL R.、TAYLOR, CHARLES P.、HERSHENSON, FRED M.、LOBBESTAEL, SAND+

  DOI：——

  日期：——
• AMINO-OXAZINES AND AMINO-DIHYDROTHIAZINE COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE
  申请人：Amgen Inc.

  公开号：EP2758406A1

  公开（公告）日：2014-07-30
• 3-Phenoxypyridine 1-oxides as anticonvulsant agents
  作者：Michael R. Pavia、Charles P. Taylor、Fred M. Hershenson、Sandra J. Lobbestael、Donald E. Butler

  DOI：10.1021/jm00399a027

  日期：1988.4

  The anticonvulsant activity of a series of 3-phenoxypyridine 1-oxides is described. An investigation carried out to optimize the activity/side effect ratio provided 4-methyl-3-phenoxypyridine 1-oxide, 3, as the derivative of choice. Overall, 3 has a pharmacological profile that is very similar to phenytoin. It exhibited significant anticonvulsant activity at doses that did not produce ataxia or sedation but caused increased spontaneous behavioral activity not seen with most anticonvulsants. The short duration of pharmacological effect of 3 was attributed to metabolic hydroxylation at the C-4 pyridine methyl group; however, structural modifications designed to inhibit this metabolic pathway were unsuccessful.