2,3-dihydro-2-(4-bromophenyl)-1,5-benzothiazepin-4(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 2,3-dihydro-2-(4-bromophenyl)-1,5-benzothiazepin-4(5H)-one
• 英文别名: 2-(4-bromophenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one；2-(4-bromophenyl)-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• 化学式: C₁₅H₁₂BrNOS
• 分子量: 334.236
• InChiKey: HFZBGKJRIMUKTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酰氯 、 2,3-dihydro-2-(4-bromophenyl)-1,5-benzothiazepin-4(5H)-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到5-acryloyl-2,3-dihydro-2-(4-bromophenyl)-1,5-benzothiazepin-4(5H)-one
  参考文献：
  名称：

  Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02254
• 作为产物：
  描述：

  对溴苯甲醛 在 哌啶 、 吡啶 、 四丁基氟化铵 作用下， 反应 26.0h， 生成 2,3-dihydro-2-(4-bromophenyl)-1,5-benzothiazepin-4(5H)-one
  参考文献：
  名称：

  Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02254

文献信息

• An efficient one-pot procedure for the synthesis of 1,5-benzothiazepinones catalyzed by tetrabutylammonium fluoride (TBAF)
  作者：Peng Zhang、Deyong Ye、Yong Chu

  DOI：10.1016/j.tetlet.2016.07.012

  日期：2016.8

  A practical and efficient method for the preparation of 1,5-benzothiazepinone derivatives in good yields has been developed using tetrabutylammonium fluoride (TBAF) as a catalyst. This study not only expands the previous work on the substrate scope and also provides more understanding of the chemistry of such drug scaffolds.

  使用四丁基氟化铵（TBAF）作为催化剂，已经开发出一种实用且有效的高产率制备1,5-苯并噻唑酮衍生物的方法。这项研究不仅扩大了以前在底物范围上的工作，而且使人们对这种药物支架的化学有了更多的了解。
• English, Robin B.; Kaye, Perry T.; Mphahlele, M. Jack, Journal of Chemical Research, Miniprint, 1995, # 10, p. 2319 - 2336
  作者：English, Robin B.、Kaye, Perry T.、Mphahlele, M. Jack、Whittal, Rory D.

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)
  作者：Peng Zhang、Hai-Rong Hu、Shi-Hui Bian、Zhao-Hui Huang、Yong Chu、De-Yong Ye

  DOI：10.1016/j.ejmech.2012.09.021

  日期：2013.3

  Glycogen synthase kinase-3 beta (GSK-3 beta) plays a key role in type II diabetes and Alzheimer's diseases, to which non-ATP competitive inhibitors represent an effectively therapeutical approach due to their good specificity. Herein, a series of small molecules benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of GSK-3 beta have been designed and synthesized. The in vitro evaluation performed by luminescent assay showed most BTZ derivatives have inhibitory effects in micromolar scale. Among them compounds 61, 6t and 6v have the IC50 values of 25.0 mu M, 27.8 mu M and 23.0 mu M, respectively. Moreover 6v is devoid of any inhibitory activity in the assays to other thirteen protein kinases. Besides, SAR is analyzed and a hypothetical enzymatic binding mode is proposed by molecular docking study, which would be useful for new candidates design. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia
  作者：Peng Zhang、Zhihui Min、Yang Gao、Jiang Bian、Xin Lin、Jie He、Deyong Ye、Yilin Li、Chao Peng、Yunfeng Cheng、Yong Chu

  DOI：10.1021/acs.jmedchem.0c02254

  日期：2021.6.10