4-phenyl-1H-imidazole-2-carboxamide | 41270-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-1H-imidazole-2-carboxamide
• 英文别名: 5-phenyl-1H-imidazole-2-carboxamide
• CAS: 41270-75-1
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: AVYBERINYRMRTR-UHFFFAOYSA-N

物化性质

• 沸点：
  466.2±38.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-1H-imidazole-2-carboxamide 在 三氯氧磷 作用下， 以 吡啶 、 二氯甲烷 、 水 为溶剂， 生成 4-phenyl-1H-imidazole-2-carbonitrile 、 N-Hydroxy-4-phenyl-1H-imidazole-2-carboximidamide
  参考文献：
  名称：

  4-aryl-thiazole derivatives

  摘要：

  该发明涉及具有以下式I的4-芳基噻唑或咪唑衍生物##STR1##其中X为0或NOH，Y为S或NR.sub.3，Ar为从苯基、萘基、四氢萘基和联苯基中选择的基团，R为独立选择的一个到四个取代基，选自氢、羟基、低烷基、低烷氧基、低硫代烷基、环烷基、卤素、CF.sub.3、NO.sub.2和O-ALK-NR.sub.1 R.sub.2，其中ALK为具有2-6个碳原子的饱和脂肪族碳氢基团，R.sub.1和R.sub.2独立地为氢或低烷基，或者与它们结合，与它们结合形成与氮原子共价的杂环，R.sub.3为氢或低烷基；或其药学上可接受的盐，但排除4-(4-氯苯基)-噻唑-2-甲酰胺。根据该发明的化合物增加心肌原纤维对钙的敏感性，并具有磷酸二酯酶抑制活性和支气管扩张活性，适用于治疗患有心力衰竭和哮喘的患者。

  公开号：

  US05254575A1
• 作为产物：
  描述：

  2-氨基丙二酰胺 、 phenyl-glyoxal-2-phenylhydrazone 反应 72.0h， 以51%的产率得到4-phenyl-1H-imidazole-2-carboxamide
  参考文献：
  名称：

  A Convenient and New One-Step Synthesis of 1H-Imidazole-2-carboxamides

  摘要：

  1,2-Diketone monophenylhydrazones (2) reacted with aminomalonamide in 1-methyl-2-pyrrolidinone to provide 1-H-imidazole-2-carboxamides (4). The condensation of 1-(4-pyridinyl)-2-propanone with phenyldiazonium chloride gave 1-phenylhydrazono-1-(4-pyridinyl)-2-propanone (2a). 4-Methyl-5-(4-pyridinyl)-1H-imidazole-2-carboxamide (4a) was converted to the corresponding nitrile (5a) by the action of phosphorous oxychloride.

  DOI：

  10.3987/com-92-6169

文献信息

• 4-aryl-imidazole derivatives
  申请人：Akzo N.V.

  公开号：US05462959A1

  公开（公告）日：1995-10-31

  The invention concerns a 4-aryl-imidazole derivative having the formula I ##STR1## wherein X is 0 or NOH, Y is NR.sub.3, Ar is a group selected from phenyl, naphthyl, tetrahydronaphthyl, and biphenyl, R is one to four substituents independently selected from hydrogen, hydroxy, lower alkyl, lower alkoxy, lower thioalkyl, cycloalkyl, halogen, CF.sub.3, NO.sub.2, and O--ALK--NR.sub.1 R.sub.2, in which ALK is a saturated aliphatic hydrocarbon group having 2-6 carbon atoms, and R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl, or form, together with the nitrogen atom to which they are bonded, a heterocyclic ring, and R.sub.3 is hydrogen or a lower alkyl; or a pharmaceutically acceptable salt thereof, with the proviso that 4-(4-chlorophenyl)-thiazole-2-carboxamide is excluded. The compounds according to the invention increase the sensitivity of cardiac myofibrils to calcium and possess phosphodiesterase inhibitory activity and bronchodilator activity, and are useful for the treatment of patients suffering from heart failure and asthma.

  本发明涉及一种具有以下式I的4-芳基咪唑衍生物： ##STR1## 其中X为0或NOH，Y为NR.sub.3，Ar为从苯基、萘基、四氢萘基和联苯基中选择的基团，R为一个到四个取代基，独立地选择自氢、羟基、低碳基、低氧基、低硫代烷基、环烷基、卤素、CF.sub.3、NO.sub.2和O-ALK-NR.sub.1 R.sub.2，其中ALK是具有2-6个碳原子的饱和脂肪族碳氢基团，R.sub.1和R.sub.2独立地为氢或低碳基，或与它们所结合的氮原子一起形成杂环环，R.sub.3为氢或低碳基；或其药学上可接受的盐，但4-(4-氯苯基)-噻唑-2-羧酰胺被排除在外。该发明的化合物增加心脏肌纤维对钙的敏感性，并具有磷酸二酯酶抑制活性和支气管扩张活性，可用于治疗患有心力衰竭和哮喘的患者。
• Benzazole derivatives, compositions, and methods of use as beta-secretase inhibitors
  申请人：Mjalli M.M. Adnan

  公开号：US20060223849A1

  公开（公告）日：2006-10-05

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及一种抑制β-淀粉样前体蛋白剪切酶（BACE）的苯并咪唑化合物，该化合物可用于治疗或预防BACE参与的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的药物组合物以及在预防或治疗BACE参与的这些疾病中使用这些化合物和组合物的用途。
• Benzazole Derivatives, Compositions, and Methods of Use as Beta-Secretase Inhibitors
  申请人：Mjalli Adnan M.M.

  公开号：US20090326006A1

  公开（公告）日：2009-12-31

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及抑制β位点淀粉样前体蛋白剪切酶（BACE）的苯并唑化合物，可用于治疗或预防BACE参与的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的药物组合物，以及在预防或治疗BACE参与的这些疾病中使用这些化合物和组合物的用途。
• Imidazole compound and process for preparing the same
  申请人：ISHIHARA SANGYO KAISHA, Ltd.

  公开号：EP0365030A1

  公开（公告）日：1990-04-25

  An imidazole compound is disclosed, which is represented by formula (I): wherein: X represents a -COOT group, in which T represents a hydrogen atom, an alkyl group, a benzyl group, or a phenyl group; or a -CONH₂ group, Y represents a hydrogen atom, a chlorine atom, or a bromine atom, Z represents an alkyl group containing from 2 to 6 carbon atoms, which may be substituted with one or more halogen atoms; or a phenyl group which may be substituted with one or more halogen atoms or alkyl groups, and Q represeents a hydrogen atom; an -SO₂R¹group, in which R¹ represents an alkyl group, a dialkylamino group, or a phenyl group which may be substituted with one or more alkyl groups; or a -CH(R²) (R³) group, in which R² represents a hydrogen atom, a methyl group, or an alkoxy group, and R³ represents an alkoxy group, an -OCH₂CH₂Si(CH₃)₃ group, or a phenyl group which may be substituted with one or more alkyl groups or alkoxy groups, provided that when Y and Q each represents a hydrogen atom and Z represents a phenyl group, X represents a group other than a -COOH group, a -COO-phenyl group, and a -CONH₂ group; and that when Y and Q each represents a hydrogen atom and Z represents an n-C₅H₁₁ group, X represents a group other than a -COOH group and a -COOC₂H₅ group. Processes for preparing imidazole compounds are also disclosed. The imidazole compounds are useful as an intermediate for production of biocides for controlling harmful organisms in the agricultural and horticultural areas, or medical and pharmaceutical fungicides.

  本发明公开了一种咪唑化合物，由式(I)表示： 其中 X代表-COOT基团，其中T代表氢原子、烷基、苄基或苯基；或代表-CONH₂基团、 Y 代表氢原子、氯原子或溴原子、 Z 代表含有 2 至 6 个碳原子的烷基，可被一个或多个卤素原子取代；或代表可被一个或多个卤素原子或烷基取代的苯基，以及 Q 代表氢原子；-SO₂R¹ 基团，其中 R¹ 代表烷基、二烷基氨基或可被一个或多个烷基取代的苯基；或-CH(R²) (R³)基团，其中 R² 代表氢原子、甲基或烷氧基，R³ 代表烷氧基、-OCH₂CH₂Si(CH₃)₃基团或可被一个或多个烷基或烷氧基取代的苯基、 条件是当 Y 和 Q 各代表一个氢原子且 Z 代表一个苯基时，X 代表一个除-COOH 基团、-COO-苯基基团和-CONH₂基团以外的基团；当 Y 和 Q 各代表一个氢原子且 Z 代表一个 n-C₅H₁₁ 基团时，X 代表一个除-COOH 基团和-COOC₂H₅基团以外的基团。 本发明还公开了制备咪唑化合物的工艺。 咪唑化合物可用作生产用于控制农业和园艺领域有害生物的杀菌剂或医用和药用杀菌剂的中间体。
• Benzazole derivatives, compositions, and methods of use as B-secretase inhibitors
  申请人：High Point Pharmaceuticals, LLC

  公开号：EP2457901A1

  公开（公告）日：2012-05-30

  The present invention is directed to benzazole compounds that inhibit β-site amyloid precursor protein-cleaving enzyme (BACE) and that may be useful in the treatment or prevention of diseases in which BACE is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which BACE is involved.

  本发明涉及抑制β位淀粉样前体蛋白切割酶（BACE）的苯甲唑化合物，这些化合物可用于治疗或预防BACE参与的疾病，如阿尔茨海默病。本发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在预防或治疗涉及 BACE 的此类疾病中的用途。