2-[2-(4-benzylpiperazin-1-yl)acetylamino]benzothiazole | 203047-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[2-(4-benzylpiperazin-1-yl)acetylamino]benzothiazole
• 英文别名: N-(1,3-benzothiazol-2-yl)-2-(4-benzylpiperazin-1-yl)acetamide
• CAS: 203047-40-9
• 化学式: C₂₀H₂₂N₄OS
• 分子量: 366.487
• InChiKey: UPUQOYWCXHKRGU-UHFFFAOYSA-N

物化性质

• 密度：
  1.298±0.06 g/cm3(Predicted)
• 溶解度：
  47.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯并噻唑 在 potassium carbonate 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-[2-(4-benzylpiperazin-1-yl)acetylamino]benzothiazole
  参考文献：
  名称：

  Targeting EGFR tyrosine kinase: Synthesis, in vitro antitumor evaluation, and molecular modeling studies of benzothiazole-based derivatives

  摘要：

  New benzothiazole-based derivatives were synthesized in the present work with the aim of evaluating their antitumor activity. They were in vitro tested against hepatocellular carcinoma (HepG2), colorectal carcinoma (HCT-116), mammary gland cancer (MCF-7), prostate cancer (PC-3), and epithelioid carcinoma (HeLa). The results of the in vitro antitumor evaluation revealed that the most active compounds were 39, 40, 51, 56, and 61 exhibiting IC50 values comparable to the reference drug lapatinib. The most active compounds were further subjected to EGFR inhibitory activity assay to rationalize their potency mode. Notably, the most active antitumor compounds 39 and 40 represented the most potent inhibitors to EGFR with IC50 values of 24.58 and 30.42 nM respectively in comparison with 17.38 nM for lapatinib as a standard drug. Molecular modeling studies were also conducted for the synthesized compounds, including docking into EGFR active site and surface mapping. Results proved the superior binding of the hydrazone derivatives 39 and 40 with EGFR suggesting them as good candidates for targeted antitumor therapy through EGFR kinase inhibition.

  DOI：

  10.1016/j.bioorg.2020.104259

文献信息

• Effect of benzothiazole/piperazine derivatives on intracerebroventricular streptozotocin-induced cognitive deficits
  作者：Ümide Demir Özkay、Özgür Devrim Can、Yusuf Özkay、Yusuf Öztürk

  DOI：10.1016/s1734-1140(12)70878-2

  日期：2012.7

  Background: In this study, benzothiazole-piperazine compounds were synthesized by condensing the functional groups of donepezil (DNP), FK-960, and sabeluzole, which are known to have therapeutic potential against Alzheimer's disease, with the aim of obtaining new and potent anti-Alzheimer agents. Methods: Initially, acetylcholinesterase/butyrylcholinesterase enzyme inhibition activities of the synthesized test compounds were investigated by Ellman's method. Effects of the compounds on a streptozotocin (STZ) model of Alzheimer's disease (SMAD) were investigated in rats. SMAD was established by intracerebroventricular (icv) injection of STZ (3 mg/kg), bilaterally. The elevated plus maze, Morris water maze, and active avoidance tests were used to examine the effects of test compounds (1, 5, and 10 mg/kg) on learning and memory parameters of icv STZ-injected rats. Effects of the test compounds on spontaneous locomotor activities of rats were examined with the activity cage test. Results: The compounds B2-B5 and DNP exhibited significant selective inhibitory potencies against acetylcholinesterase. Compounds B2 and B3 at 10 mg/kg doses and compounds B4 and B5 at 5 and 10 mg/kg doses, as well as the reference drug DNP (1 and 3 mg/kg), significantly improved the learning and memory parameters of animals in all cognition tests. None of the test compounds changed spontaneous locomotor activities. Conclusion: Results of the present study revealed that compounds B2-B5 repaired the parameters related to the learning and memory deficits of icv STZ-injected rats. Potencies of these test compounds were comparable to the activity of DNP.
• US5731438A
  申请人：——

  公开号：US5731438A

  公开（公告）日：1998-03-24
• US5780241A
  申请人：——

  公开号：US5780241A

  公开（公告）日：1998-07-14
• US5798360A
  申请人：——

  公开号：US5798360A

  公开（公告）日：1998-08-25
• US5817489A
  申请人：——

  公开号：US5817489A

  公开（公告）日：1998-10-06