2,4-dibromo-7,8,9,10-tetrahydroazepino<2,1-b>quinazolin-12(6H)-one | 122229-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,4-dibromo-7,8,9,10-tetrahydroazepino<2,1-b>quinazolin-12(6H)-one
• 英文别名: 2,4-dibromo-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-one；2,4-dibromo-7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one；2,4-dibromo-7,8,9,10-tetrahydro-6H-azepino[2,1-b]quinazolin-12-one
• CAS: 122229-02-1
• 化学式: C₁₃H₁₂Br₂N₂O
• 分子量: 372.059
• InChiKey: RNMAEPHNDZMZJB-UHFFFAOYSA-N

物化性质

• 熔点：
  168.3 °C(Solv: acetone (67-64-1))
• 沸点：
  480.6±55.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dibromo-7,8,9,10-tetrahydroazepino<2,1-b>quinazolin-12(6H)-one 在 氢溴酸 、 potassium carbonate 、 copper dichloride 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 96.0~120.0 ℃ 、565.37 kPa 条件下， 反应 34.0h， 生成 2,4-二乙氧基-7,8,9,10-四氢氮杂卓并[2,1-b]喹唑啉-12(6H)-酮
  参考文献：
  名称：

  Synthesis and bronchodilator activity of new quinazolin derivative

  摘要：

  Taking lead from a naturally occurring quinazolin vasicine, a number of compounds were developed and evaluated for bronchodilator and anti-allergic activities. One of these compounds was 2,4-diethoxy-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-one, hereinafter named 95-4, exhibited marked bronchodilator activity evaluated on contracted trachea or constricted tracheo-bronchial tree. On intestinal smooth muscle too it showed relaxant effect. Trachea] relaxant effect was not found to be mediated through beta-adrenoceptors. Cumulative dose-response study with acetylcholine and histamine indicated for its non-specific direct effect on smooth muscles. 95-4 was found to be more potent than theophylline and less to that of salbutamol on dose basis. Tested by a number of experimental models, it was found devoid of anti-allergic activity. It was also found to be free from any adverse effect.95-4 due to its marked bronchial muscle relaxant effect can find use in conditions associated with spasm of bronchial muscles. (c) 2006 Published by Elsevier SAS.

  DOI：

  10.1016/j.ejmech.2005.09.010
• 作为产物：
  描述：

  7,8,9,10-四氢氮杂卓并(2,1-b)喹唑啉-12(6H)-酮 在 sodium tetrahydroborate 、 溴 作用下， 以 四氯化碳 、 乙醇 为溶剂， 生成 2,4-dibromo-7,8,9,10-tetrahydroazepino<2,1-b>quinazolin-12(6H)-one
  参考文献：
  名称：

  azepino [2,1-b]喹唑啉酮的镇咳作用

  摘要：

  摘要合成了一系列阿塞匹诺[2,1-b]喹唑啉酮（C-1 – C-16），并使用柠檬酸诱导的豚鼠咳嗽模型评估了它们的镇咳活性。化合物C-1 – C-16引起柠檬酸引起的咳嗽频率显着降低和咳嗽潜伏期延长。C-3[2,4-dibromo-7,8,9,10-tetrahydroazepino [2,1-b] quinazolin-12（6H）-one]与可待因（10 mg / kg）相比具有明显的镇咳作用。在A和B环上进行了各种取代，发现除溴以外的所有取代基（如甲氧基，羟基，硝基，氨基（环A）和烷基，乙酰基，苯甲酰基（环B））均会降低未取代的7,8 ，9,10-四氢阿斯匹诺[2,1-b]喹唑啉-12（6H）-作为镇咳药。 图形概要合成了一系列阿塞匹诺[2,1-b]喹唑啉酮，并使用柠檬酸诱导的豚鼠咳嗽模型评估了镇咳活性。

  DOI：

  10.1007/s00044-011-9641-1

文献信息

• Malhotra; Koul; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1, p. 100 - 104
  作者：Malhotra、Koul、Singh、Singh、Dhar

  DOI：——

  日期：——
• MALHOTRA, S.;KOUL, S. K.;SINGH, S.;SINGH, G. B.;DHAR, K. L., INDIAN J. CHEM. B , 28,(1989) N, C. 100-104
  作者：MALHOTRA, S.、KOUL, S. K.、SINGH, S.、SINGH, G. B.、DHAR, K. L.

  DOI：——

  日期：——
• Synthesis and bronchodilator activity of new quinazolin derivative
  作者：A. Zabeer、A. Bhagat、O.P. Gupta、G.D. Singh、M.S. Youssouf、K.L. Dhar、O.P. Suri、K.A. Suri、N.K. Satti、B.D. Gupta、G.N. Qazi

  DOI：10.1016/j.ejmech.2005.09.010

  日期：2006.3

  Taking lead from a naturally occurring quinazolin vasicine, a number of compounds were developed and evaluated for bronchodilator and anti-allergic activities. One of these compounds was 2,4-diethoxy-6,7,8,9,10,12-hexahydroazepino[2,1-b]quinazolin-12-one, hereinafter named 95-4, exhibited marked bronchodilator activity evaluated on contracted trachea or constricted tracheo-bronchial tree. On intestinal smooth muscle too it showed relaxant effect. Trachea] relaxant effect was not found to be mediated through beta-adrenoceptors. Cumulative dose-response study with acetylcholine and histamine indicated for its non-specific direct effect on smooth muscles. 95-4 was found to be more potent than theophylline and less to that of salbutamol on dose basis. Tested by a number of experimental models, it was found devoid of anti-allergic activity. It was also found to be free from any adverse effect.95-4 due to its marked bronchial muscle relaxant effect can find use in conditions associated with spasm of bronchial muscles. (c) 2006 Published by Elsevier SAS.
• Antitussive effects of azepino[2,1-b]quinazolones
  作者：Kunal Nepali、Mukunda S. Bande、Sameer Sapra、Atul Garg、Sunil Kumar、Punita Sharma、Rohit Goyal、Naresh Kumar Satti、Om Parkash Suri、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9641-1

  日期：2012.7

  (10 mg/kg). Various substitutions were made at Rings A and B, and all substituents like methoxy, hydroxyl, nitro, amino (Ring A) and alkyl, acetyl, benzoyl (Ring B) other than bromine were found to reduce the potential of the unsubstituted 7,8,9,10-tetrahydroazepino[2,1-b]quinazolin-12(6H)-one as antitussive. Graphical AbstractA series of azepino[2,1-b]quinazolones has been synthesized and evaluated for antitussive

  摘要合成了一系列阿塞匹诺[2,1-b]喹唑啉酮（C-1 – C-16），并使用柠檬酸诱导的豚鼠咳嗽模型评估了它们的镇咳活性。化合物C-1 – C-16引起柠檬酸引起的咳嗽频率显着降低和咳嗽潜伏期延长。C-3[2,4-dibromo-7,8,9,10-tetrahydroazepino [2,1-b] quinazolin-12（6H）-one]与可待因（10 mg / kg）相比具有明显的镇咳作用。在A和B环上进行了各种取代，发现除溴以外的所有取代基（如甲氧基，羟基，硝基，氨基（环A）和烷基，乙酰基，苯甲酰基（环B））均会降低未取代的7,8 ，9,10-四氢阿斯匹诺[2,1-b]喹唑啉-12（6H）-作为镇咳药。 图形概要合成了一系列阿塞匹诺[2,1-b]喹唑啉酮，并使用柠檬酸诱导的豚鼠咳嗽模型评估了镇咳活性。