7-氯-3,4-二氢-1H-苯并[E][1,4]二氮杂卓-2,5-二酮 | 5177-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 7-氯-3,4-二氢-1H-苯并[E][1,4]二氮杂卓-2,5-二酮
• 中文别名: 7-氯-3,4-二氢-1H-苯并[e][1,4]二氮杂环庚烷-2,5-二酮；7-氯-3,4-二氢-1H-苯并[e][1,4]二氮杂卓-2,5-二酮
• 英文名称: 7-chloro-3H-1,4-benzodiazepin-(1H,4H)-2,5-dione
• 英文别名: 7-chloro-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione；7-chloro-2,5-dioxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine；7-Chlor-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,5-dion；7-Chlor-3,4-dihydro-1H-1,4-benzodiazepin-2,5-dion；7-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione；7-chloro-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione；7-chloro-2,3,5-trihydro-1H,4H-1,4-benzodiazepine-2,5-dione；7-Chlor-3H-1,4-benzodiazepin-2,5(1H,4H)-dion；Chloro-7-(1,3,4H)-benzodiazepin-1,4-dion-2,5
• CAS: 5177-39-9
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: DUAONSMGNHXBMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 储存条件：
  2-8°C，密封保存，置于干燥处。

反应信息

• 作为反应物：
  描述：

  7-氯-3,4-二氢-1H-苯并[E][1,4]二氮杂卓-2,5-二酮 在 盐酸 、 lithium aluminium tetrahydride 、 TEA 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 1-(1-Amino-7-chloro-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-ethanone
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100
• 作为产物：
  描述：

  5-氯靛红酸酐 在 吡啶 、 溶剂黄146 作用下， 反应 48.0h， 生成 7-氯-3,4-二氢-1H-苯并[E][1,4]二氮杂卓-2,5-二酮
  参考文献：
  名称：

  Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor

  摘要：

  Evaluation of selected compounds from our Corporate Compound Library in a human 5-HT2C receptor binding assay led to the discovery of WAY-629, a cyclohexyl[b][1,4]benzodiazepinoindole (K-i 56nM, E-max 90%), which is selective for the 5-HT2C receptor versus other serotonin receptor subtypes, and dopamine, histamine, adrenergic, and muscarinic receptors. In addition, WAY-629 was active in vivo in a rat model of feeding behavior. An SAR study based on WAY-629 led to compound 11 (K-i 13 nM, E-max 102%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.100
• 作为试剂：
  描述：

  、 苯并二氮杂卓 、 吡啶 、 5-氯靛红酸酐 在 7-氯-3,4-二氢-1H-苯并[E][1,4]二氮杂卓-2,5-二酮 作用下， 以 甘氨酸甲酯盐酸盐 为溶剂， 以the final product 7-chloro-2,5-dioxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (compound 3B) is formed的产率得到
  参考文献：
  名称：

  BENZODIAZEPINE DERIVATIVE AND METHOD OF PRODUCING THE SAME

  摘要：

  一种苯二氮平衍生物及其制备方法，使用异噁唑酐或5-氯异噁唑酐与氨基酸酯盐进行简单的环化反应，直接获得低副产物百分比的产物，无需进行复杂的柱层析分离和纯化过程，且含氯结构可以提高脂溶性和氯离子渗透性，允许放射性同位素的功能团修饰，以最大化中枢神经系统镇静、抗惊厥和抗痉挛等药理特性的效果，或将苯二氮平衍生物用作具有优异应用效果的系统对比剂。

  公开号：

  US20150252009A1

文献信息

• [1,4]Diazepino[6,7,1-ij]quinoline derivatives as antipsychotic and antiobesity agents
  申请人：Wyeth

  公开号：US20040009970A1

  公开（公告）日：2004-01-15

  Compounds of Formula I or a pharmaceutically acceptable salt thereof are provided: 1 where R 1 through R 7 are defined herein. The compounds of Formula I are 5HT2c agonists or partial agonists, and are useful for treating a variety of disorders.

  提供公式I的化合物或其药用可接受的盐：其中R1至R7在此处定义。公式I的化合物是5HT2c受体激动剂或部分激动剂，可用于治疗多种疾病。
• Glycine receptor antagonist pharmacophore
  申请人：State of Oregon, Acting by and through the Oregon State Board of Higher

  公开号：US05597922A1

  公开（公告）日：1997-01-28

  Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.

  通过向需要此类治疗的动物投药，揭示了治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失的方法，以及治疗包括阿尔茨海默病、肌萎缩侧索硬化症、亨廷顿病和唐氏综合症在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度活跃的不良后果，以及治疗焦虑、慢性疼痛、惊厥和诱导麻醉的方法是通过给予具有高结合到甘氨酸受体的化合物。
• [EN] BENZODIAZEPINONE COMPOUNDS AND METHODS OF TREATMENT USING SAME<br/>[FR] COMPOSÉS DE BENZODIAZÉPINONE ET MÉTHODES DE TRAITEMENT LES UTILISANT
  申请人：UNIV MICHIGAN

  公开号：WO2011035124A1

  公开（公告）日：2011-03-24

  The invention provides 1,4-benzodiazepinone compounds, pharmaceutical compositions, and methods of treating autoimmune disorders, chronic inflammatory disorders, and hyperproliferative disorders. For example, the 1,4-benzodiazepinone compounds and pharmaceutical compositions are contemplated to be useful for treating rheumatoid arthritis, graft-versus-host disease, inflammatory bowel disease, and the like.

  该发明提供了1,4-苯并二氮杂酮化合物、药物组合物以及治疗自身免疫性疾病、慢性炎症性疾病和过度增殖性疾病的方法。例如，这些1,4-苯并二氮杂酮化合物和药物组合物被认为对治疗类风湿关节炎、移植物抗宿主病、炎症性肠病等疾病有用。
• [1,4]Diazepino [6,7,1-jk] carbazoles and derivatives
  申请人：American Home Products Corporation

  公开号：US20020086860A1

  公开（公告）日：2002-07-04

  This invention provides [1,4]diazepino[6,7,1-jk]carbazole compounds of the formula: 1 wherein: R 1 and R 2 are H, alkyl, alkoxy, halogen, fluorinated alkyl, —CN, —NH—SO 2 -alkyl, —SO 2 —NH-alkyl, alkyl amide, amino, alkylamino, dialkylamino, fluorinated alkoxy, acyl, phenoyl or thiophenoyl; R 3 , R 4 , R 5 and R 6 are H, alkyl, cycloalkyl, alkoxy or cycloalkoxy; R 7 is H or alkyl; R 8 is H or alkyl; and the dashed line indicates an optional double bond; or a pharmaceutically acceptable salt thereof, as well as methods and pharmaceutical compositions utilizing them for the treatment or prevention of disorders such as obsessive-compulsive disorder, depression, anxiety, schizophrenia, migraine, sleep disorders, eating disorders, obesity, epilepsy, and spinal cord injury.

  这项发明提供了一种公式为1的[1,4]二氮杂二环[6,7,1-jk]吲哚类化合物，其中：R1和R2为H、烷基、烷氧基、卤素、氟代烷基、—CN、—NH—SO2-烷基、—SO2—NH-烷基、烷基酰胺、氨基、烷基氨基、二烷基氨基、氟代烷氧基、酰基、苯甲酰基或硫代苯甲酰基；R3、R4、R5和R6为H、烷基、环烷基、烷氧基或环烷氧基；R7为H或烷基；R8为H或烷基；虚线表示可选的双键；或其药学上可接受的盐，以及利用它们用于治疗或预防强迫症、抑郁症、焦虑症、精神分裂症、偏头痛、睡眠障碍、饮食障碍、肥胖症、癫痫和脊髓损伤等疾病的方法和药物组合物。
• A NOVEL ONE STEP APPROACH TO THE SYNTHESIS OF 3H-1,4-BENZODIAZEPIN-(1H,4H)-2,5-DIONES FROM 1,2,3-BENZOTRIAZIN-4-(3H)-ONE.
  作者：Renu Gupta、Reenu Sirohi、Sudha Shastri、D. Kishore

  DOI：10.1515/hc.2003.9.4.363

  日期：2003.1

  hydrolytic cleavage of N2-N3 bond to give rise to the transient formation of a diazonium compound which in appropriately substituted 3 is amenable further to products through the intra or intermolecular condensations. RESULTS AND DISCUSSION 1,2,3Benzotriazin-4-(3H)-ones (3) are most intensively studied class of 1,2,3-benzotriazine derivatives and effective method for their synthesis are known. The most

  l,2,3-苯并三嗪-4-(3H)-one(3)及其6-氯衍生物(4)与α-氨基酸热缩合产生3H-1,4-苯并二氮杂-(1H,4H)- 2,5-二酮(7-12) 的产率适中。环缩合被认为是通过形成亚胺烯酮中间体 (5) 进行的。引言 1,4-苯二氮卓类及其氧代衍生物代表了一类具有广泛精神药理学特性的活性化合物。我们寻求为 1,4 苯二氮卓合成开发新的一步策略，这使我们研究了具有经证实的合成潜力的材料在其合成中的应用。对文献的搜索表明，l,2,3-benzotriazin-4-(3H)-one (3) 具有非凡的能力，可以用酸、碱和在没有这些的情况下裂解其含氮环，在热条件下得到中间体苯并氮杂 5，该中间体已广泛用于合成。这促使我们研究其在 1,4-苯二氮卓合成中的应用。除了 Nesmeyanov 及其同事在 1973 年使用 30% 磷酸将 1 转化为 2（方案 1）的一次尝试之外，之前似乎没有其他尝试探索