3-Formylaminomethyl-5-cyclopropyl-1,2,4-oxadiazole | 106447-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Formylaminomethyl-5-cyclopropyl-1,2,4-oxadiazole
• 英文别名: 5-cyclopropyl-3-formylamino-methyl-1,2,4-oxadiazole；5-cyclopropyl-3-formylaminomethyl-1,2,4-oxadiazole；N-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]formamide
• CAS: 106447-63-6
• 化学式: C₇H₉N₃O₂
• 分子量: 167.167
• InChiKey: OYPIXUZKTODLAC-UHFFFAOYSA-N

物化性质

• 沸点：
  425.4±47.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Formylaminomethyl-5-cyclopropyl-1,2,4-oxadiazole 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-Cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole
  参考文献：
  名称：

  High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

  DOI：

  10.1021/jm940765f
• 作为产物：
  描述：

  环丙基甲酰氯 、 N-formylaminoacetamide oxime 在 水 、 三乙胺 作用下， 生成 3-Formylaminomethyl-5-cyclopropyl-1,2,4-oxadiazole
  参考文献：
  名称：

  High-Affinity Partial Agonist Imidazo[1,5-a]quinoxaline Amides, Carbamates, and Ureas at the γ-Aminobutyric Acid A/Benzodiazepine Receptor Complex

  摘要：

  A series of imidazo[1,5-alpha]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies racing from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

  DOI：

  10.1021/jm940765f

文献信息

• Oxadiazolylimidazobenzodiazepine, compositions, and method
  申请人：AS Ferrosan

  公开号：US04622320A1

  公开（公告）日：1986-11-11

  The application discloses novel benzodiazepine agonist compounds, namely, 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-5,6-dihydro-5-methyl-6-oxo-7-halo-4 H-imidazo [1,5-a][1,4]benzodiazepines, pharmaceutical compositions thereof, and a method of ameliorating central nervous system ailments therewith, especially convulsions and anxiolytic states. A novel intermediate and process for their production are also disclosed.

  该申请公开了新型苯二氮卓类激动剂化合物，即3-(5-环丙基-1,2,4-噁二唑-3-基)-5,6-二氢-5-甲基-6-酮-7-卤代-4 H-咪唑[1,5-a][1,4]苯二氮卓类化合物，以及其药物组合物，以及用于改善中枢神经系统疾病，特别是抽搐和抗焦虑状态的方法。还公开了一种新型中间体和其生产方法。
• Imidazoquinoxaline compounds and their preparation and use
  申请人：A/S Ferrosan

  公开号：US04968682A1

  公开（公告）日：1990-11-06

  New imidazoquinoxaline compounds having the general formula ##STR1## wherein ##STR2## wherein R' is C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.1-6 -alkoxymethyl; and ##STR3## wherein R.sup.5 is hydrogen or halogen. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and in improving the cognitive function of the brain of mammals.

  新的咪唑喹喔喹啉类化合物具有以下一般式##STR1##其中##STR2##其中R'为C.sub.1-6-烷基，C.sub.3-7-环烷基或C.sub.1-6-烷氧甲基；以及##STR3##其中R.sup.5为氢或卤素。这些化合物在精神药物制剂中作为抗惊厥药、抗焦虑药、催眠药以及改善哺乳动物大脑认知功能方面具有用途。
• 3-substituted-4,5-dihydro-5-oxo imidazoquinazolines, their preparation,
  申请人：A/S Ferrosan

  公开号：US04771051A1

  公开（公告）日：1988-09-13

  New heterocyclic compounds having the general formula ##STR1## wherein X is ##STR2## or CO.sub.2 R' wherein R' is C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl, or C.sub.3-7 -cycloalkylmethyl, R.sup.6 and R.sup.7 independently are hydrogen, halogen, alkoxy, or trifluoromethyl, and R" is hydrogen, C.sub.1-6 -alkyl, or C.sub.3-7 -cycloalkyl. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.

  具有一般式##STR1##的新杂环化合物，其中X为##STR2##或CO.sub.2 R'，其中R'为C.sub.1-6-烷基，C.sub.3-7-环烷基或C.sub.3-7-环烷基甲基，R.sup.6和R.sup.7独立地为氢，卤素，烷氧基或三氟甲基，而R"为氢，C.sub.1-6-烷基或C.sub.3-7-环烷基。这些化合物在精神药物制剂中作为抗癫痫药、抗焦虑药、催眠药和脑功能改善药物中有用。
• Imidazothienopyrimidines useful in psychopharmaceutical preparations
  申请人：A/S Ferrosan

  公开号：US04866065A1

  公开（公告）日：1989-09-12

  New heterocyclic compounds having the general formula ##STR1## wherein ##STR2## wherein R' is C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.1-6 -alkoxymethyl; R.sup.4 is C.sub.1-6 -alkyl; --S-- is ##STR3## and wherein R.sup.5 and R.sup.6 independently are hydrogen, C.sub.1-6 -alkyl, or aryl. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and in improving the cognitive function of the brain of mammals.

  具有一般公式的新杂环化合物##STR1##其中##STR2##其中R'为C.sub.1-6-烷基，C.sub.3-7-环烷基或C.sub.1-6-烷氧甲基；R.sup.4为C.sub.1-6-烷基；--S--为##STR3##其中R.sup.5和R.sup.6独立地为氢，C.sub.1-6-烷基或芳基。这些化合物在精神药物制剂中作为抗癫痫药、抗焦虑药、催眠药以及改善哺乳动物大脑认知功能方面具有用途。
• Oxadiazolyl imidazobenzodiazepine derivatives pharmaceutical
  申请人：A/S Ferrosan

  公开号：US04670433A1

  公开（公告）日：1987-06-02

  New oxadiazolyl imidazobenzodiazepine derivatives having the formula ##STR1## wherein R.sup.3 has the formula ##STR2## wherein R" is hydrogen, C.sub.1-6 alkyl C.sub.1-6 alkoxymethyl or C.sub.3-6 - cycloalkyl; R.sup.4 is hydrogen; R.sup.5 is C.sub.1-6 alkyl or R.sup.4 and R.sup.5 together form a 2-4 membered alkylene bridge; and R.sup.A is C.sub.1-6 alkyl, C.sub.1-6 alkoxy, or C.sub.1-3 trifluoroalkyl, pharmaceutical compositions thereof, and method of treating therewith, are disclosed. The compounds and pharmaceutical compositions are useful in the amelioration, mitigation, or elimination of central nervous system disorders related to benzodiazepine receptors and especially as anticonvulsants, anxiolytics, hypnotics, and nootropics.

  新的氧代二唑基咪唑苯二氮䓬啉衍生物具有以下结构式：其中R.sup.3具有以下结构式：其中R"为氢、C.sub.1-6烷基、C.sub.1-6烷氧甲基或C.sub.3-6环烷基；R.sup.4为氢；R.sup.5为C.sub.1-6烷基或R.sup.4和R.sup.5共同形成2-4成员的烷基桥；R.sup.A为C.sub.1-6烷基、C.sub.1-6烷氧基或C.sub.1-3三氟烷基，公开了这些化合物、药物组合物以及用于治疗的方法。这些化合物和药物组合物在改善、缓解或消除与苯二氮䓬啉受体相关的中枢神经系统疾病方面具有用途，特别是作为抗惊厥药、抗焦虑药、催眠药和智力增强药。