3-(isocyanomethyl)-5-tert-butyl-1,2,4-oxadiazole | 148890-56-6

• 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-(isocyanomethyl)-5-tert-butyl-1,2,4-oxadiazole
• 英文别名: 5-tert-butyl-3-isocyanomethyl-1,2,4-oxadiazole；5-tert-butyl-3-isocyano-1,2,4-oxadiazole；5-(1,1-dimethyl)ethyl-3-isocyanomethyl-1,2,4-oxadiazole；5-(1,1-Dimethylethyl)-3-isocyanomethyl-1,2,4-oxadiazole；5-tert-butyl-3-(isocyanomethyl)-1,2,4-oxadiazole
• CAS: 148890-56-6
• 化学式: C₈H₁₁N₃O
• 分子量: 165.195
• InChiKey: ITEYWZLPBZPHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3a-dihydro1H-oxazolo<3,4-a>quinoxaline-1,4(5H)-dione 、 3-(isocyanomethyl)-5-tert-butyl-1,2,4-oxadiazole 生成 (S)-1-[5-(1,1-Dimethylethyl)-1,2,4-oxadiazol-3-yl ]-12,12a-dihydroimidazo[1,5-a]pyrrolo[2,1-c]quinoxalin-10(11H)-one
  参考文献：
  名称：

  Imidazo[1,5-A]quinoxalines

  摘要：

  一种涉及咪唑并[1,5-a]喹喔啉(I)的发明，不含内环羰基，并且可用作抗焦虑和镇静/催眠剂。

  公开号：

  US05541324A1
• 作为产物：
  描述：

  3-<(N-formylamino)methyl>-5-tert-butyl-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， 以85%的产率得到3-(isocyanomethyl)-5-tert-butyl-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

• Studies on the chemistry of thienoannelated<i>O,N</i>- and<i>S,N</i>-containing heterocycles. 24 [1]. Synthesis of imidazo[1,5-<i>d</i>]thieno[2,3-<i>b</i>][1,4]-thiazine derivatives as potential receptor ligands
  作者：Thomas Erker、Norbert Handler

  DOI：10.1002/jhet.5570390407

  日期：2002.7

  A facile synthesis of the imidazo[1,5-d]thieno[2,3-b][1,4]thiazine ring system is described. Reaction of 6-benzyl-2,3-dihydro-1H-thieno[2,3-b][1,4]thiazine-2-one (1) with potassium tert-butoxide and diethylchlorophosphate gave intermediate 2 which resulted in the disired ring system after adding the corresponding isocyanides and potassium tert-butoxide.

  描述了咪唑并[1,5- d ]噻吩并[2,3- b ] [1,4]噻嗪环系统的简便合成方法。的6-苄基-2,3-二氢-1-反应ħ -噻吩并[2,3- b ] [1,4]噻嗪-2-酮（1）与钾叔丁醇和氯磷酸二乙酯，得到中间体2，其导致加入相应的异氰化物和叔丁醇钾后，形成不想要的环系统。
• Synthesis of a New Series of Imidazo-[1,5-a]pyrido[2,3-e]pyrazines as Potential Ligands for the GABA Receptor Complex
  作者：Manuela Weber、Herbert Bartsch、Thomas Erker

  DOI：10.1007/s007060200037

  日期：2002.5.1

  -butoxide and diethyl chlorophosphate to afford an intermediate dihydropyrido[2,3- b ]pyrazin-2-ylphosphate derivative which in turn furnished the desired 1,2,4-oxadiazolylimidazo[1,5- a ]pyrido[2,3- e ]pyrazine derivatives with 5-alkyl-3-isocyanomethyl-1,2,4-oxadiazoles in the presence of additional tert -butoxide. The title compounds are potential ligands for the γ-aminobutyric acid A/benzodiazepine receptor

  从2-氯-3-硝基吡啶开始，合成2-异丙基-1，4-二氢吡啶并[2，3 - b ]吡嗪-2（ 3H ），3-二酮。将该化合物与 叔 丁醇钾和氯代磷酸二乙酯反应， 得到中间体二氢吡啶并[2,3 - b ]吡嗪-2-基磷酸酯衍生物，进而提供所需的1,2,4-恶二唑基咪唑并[1,5- a ]在另外的 叔 丁醇盐存在下，将吡啶并[2,3- e ]吡嗪衍生物与5-烷基-3-异氰基甲基-1,2,4-恶二唑合成 。标题化合物是γ-氨基丁酸A /苯并二氮杂receptor受体复合物的潜在配体。
• Imidazo[1,5-A]quinolines for treatment of anxiety and sleep disorders
  申请人：The Upjohn Company

  公开号：US05594140A1

  公开（公告）日：1997-01-14

  Imidazo[1,5-a]quinolines of formula (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders. ##STR1##

  化学式为(I)的咪唑并[1,5-a]喹啉是治疗焦虑、睡眠障碍、惊恐状态、癫痫和肌肉疾病的有用药物。##STR1##
• Imidazo\x9b1,5-a!quinolines for treatment of anxiety and sleep disorders
  申请人：Pharmacia & Upjohn Company

  公开号：USRE035840E1

  公开（公告）日：1998-07-07

  The present invention is to imidazo\x9b1,5-a!quinolines (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.

  本发明涉及咪唑并[1,5-a]喹啉（I），其是治疗焦虑、睡眠障碍、惊恐状态、抽搐和肌肉疾病的有用药物。
• Use of imidazo\x9b1,5-a!quinolones as neuroprotective agents
  申请人：Pharmacia & Upjohn Company

  公开号：US05935970A1

  公开（公告）日：1999-08-10

  The imidazo\x9b1,5-a!quinolines (I) are useful in treating neurological diseases/conditions or chronic neurodegenerative diseases/conditions.

  咪唑[1,5-a]喹啉（I）在治疗神经疾病/症或慢性神经退行性疾病/症方面具有用处。