7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one | 42239-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one
• 英文别名: 7-chloro-5,10-dihydro-benzo[b]thieno[2,3-e]azepin-4-one；7-Chloro-5,10-dihydrothieno[3,2-c][1]benzazepin-4-one
• CAS: 42239-54-3
• 化学式: C₁₂H₈ClNOS
• 分子量: 249.721
• InChiKey: HEVAELVAXIINKK-UHFFFAOYSA-N

物化性质

• 熔点：
  264-266 °C(Solvent: Acetone)
• 沸点：
  315.8±42.0 °C(predicted)
• 密度：
  1.404±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 7-chloro-4-piperazin-1-yl-10H-thieno[3,2-c][1]benzazepine
  参考文献：
  名称：

  Hunziker; Fischer; Kipfer, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 391 - 398

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(4-Chloro-2-isocyanatophenyl)methyl]thiophene 在 PPA 作用下， 反应 1.0h， 生成 7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one
  参考文献：
  名称：

  Hunziker; Fischer; Kipfer, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 391 - 398

  摘要：

  DOI：

文献信息

• A Modular Approach to Dibenzo‐fused ϵ‐Lactams: Palladium‐Catalyzed Bridging‐C−H Activation
  作者：Yinghua Yu、Liyao Ma、Jiajin Xia、Luoting Xin、Lei Zhu、Xueliang Huang

  DOI：10.1002/anie.202007799

  日期：2020.10.5

  Tricyclic ring systems possessing a dibenzo structure joined to a seven‐membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium‐catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described

  具有连接到七元杂环的二苯并结构的三环系统经常表现出重要的生物学活性。然而，缺乏基于易于获得的化学物质的有效分子间反应的针对这些分子的模块化方法。在这里，描述了史无前例的钯催化形式的[4 + 3]环状结构，用于这些三环系统的模块化结构。该反应具有易于获得的反应物（邻卤代芳基醛和N甲苯磺酰基hydr），广泛的底物范围和出色的官能团相容性。易于扩大规模的反应，复杂分子的后期修饰以及生物活性分子和批准药物的集体合成证明了合成潜力。
• Behavioral Approach to Nondyskinetic Dopamine Antagonists:  Identification of Seroquel
  作者：Edward J. Warawa、Bernard M. Migler、Cyrus J. Ohnmacht、Ann L. Needles、George C. Gatos、Frances M. McLaren、Cynthia L. Nelson、Karen M. Kirkland

  DOI：10.1021/jm000242+

  日期：2001.2.1

  A great need exists for antipsychotic drugs which will not induce extrapyramidal symptoms (EPS) and tardive dyskinesias (TDs). These side effects are deemed to be a consequence of nonselective blockade of nigrostriatal and mesolimbic dopamine D2 receptors. Nondyskinetic clozapine (1) is a low-potency D2 dopamine receptor antagonist which appears to act selectively in the mesolimbic area. In this work dopamine antagonism was assessed in two mouse behavioral assays: antagonism of apomorphine-induced climbing and antagonism of apomorphine-induced disruption of swimming. The potential for the liability of dyskinesias was determined in haloperidol-sensitized Cebus monkeys. Initial examination of a few close cogeners of 1 enhanced confidence in the Cebus model as a predictor of dyskinetic potential. Considering dibenzazepines, 2 was not dyskinetic whereas 2a was dyskinetic. Among dibenzodiazepines, 1 did not induce dyskinesias where as its N-2-(2-hydroxyethoxy)ethyl analogue 3 was dyskinetic. The emergence of such distinctions presented an opportunity. Thus, aromatic and N-substituted analogues of 6-(piperazin-1-yl)-11H-dibenz[b,e]azepines and 11-(piperazin-1-yl)dibenzo[b,f][1,4]thiazepines and -oxazepines were prepared and evaluated. 11-(4-[2-(2-Hydroxyethoxy)ethyl]piperazin-1-yl)dibenzo[b,f][1,4]thiazepine (23) was found to be an apomorphine antagonist comparable to clozapine. It was essentially nondyskinetic in the Cebus model. With 23 as a platform, a number of N-substituted analogues were found to be good apomorphine antagonists but all were dyskinetic.
• HUNZIKER, F.;FISCHER, R.;KIPFER, P.;SCHMUTZ, J.;BUERKI, H. R.;FICHENBERGE+, EUR. J. MED. CHEM.-CHIM. THER., 1981, 16, N 5, 391-398
  作者：HUNZIKER, F.、FISCHER, R.、KIPFER, P.、SCHMUTZ, J.、BUERKI, H. R.、FICHENBERGE+

  DOI：——

  日期：——
• US3962248A
  申请人：——

  公开号：US3962248A

  公开（公告）日：1976-06-08
• Hunziker; Fischer; Kipfer, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 391 - 398
  作者：Hunziker、Fischer、Kipfer、et al.

  DOI：——

  日期：——