6-Bromo-4-ethyl-1,3-benzothiazol-2-amine | 383131-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-Bromo-4-ethyl-1,3-benzothiazol-2-amine
• CAS: 383131-52-0
• 化学式: C₉H₉BrN₂S
• mdl: MFCD02663856
• 分子量: 257.154
• InChiKey: RLRFPJSDSWJTIX-UHFFFAOYSA-N

物化性质

• 沸点：
  389.2±34.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Bromo-4-ethyl-1,3-benzothiazol-2-amine 在 吡啶 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 12.17h， 生成 N-(6-(3,5-dimethylisoxazol-4-yl)-4-ethylbenzo[d]thiazol-2-yl)-2,4,6-trifluorobenzenesulfonamide
  参考文献：
  名称：

  10.1002/cplu.202400234

  摘要：

  AbstractComputational techniques accelerate drug discovery by identifying bioactive compounds for specific targets, optimizing molecules with moderate activity, or facilitating the repositioning of inactive items onto new targets. Among them, the Inverse Virtual Screening (IVS) approach is aimed at the evaluation of one or a small set of molecules against a panel of targets for addressing target identification. In this work, a focused library of benzothiazole‐based compounds was re‐investigated by IVS. Four items, originally synthesized and tested on bromodomain‐containing protein 9 (BRD9) but yielding poor binding, were critically re‐analyzed, disclosing only a partial fit with 3D structure‐based pharmacophore models, which, in the meanwhile, were developed for this target. Afterwards, these compounds were re‐evaluated through IVS on a panel of proteins involved in inflammation and cancer, identifying soluble epoxide hydrolase (sEH) as a putative interacting target. Three items were subsequently confirmed as able to interfere with sEH activity, leading to inhibition percentages spanning from 70 % up to 30 % when tested at 10 μM. Finally, one benzothiazole‐based compound emerged as the most promising inhibitor featuring an IC50 in the low micromolar range (IC50=6.62±0.13 μM). Our data confirm IVS as a predictive tool for accelerating the target identification and repositioning processes.

  DOI：

  10.1002/cplu.202400234

文献信息

• Synthesis, Spectral Characterization and Biological Evaluation of New Substituted 2H-Pyrimido[2,1-b]benzothiazol-2-ones
  作者：Kshamta Goyal、Shikha Agarwal、Dinesh Agarwal、Naveen Gautam、D.C. Gautam

  DOI：10.2174/1570178614666161115163142

  日期：2017.1.3

  current years. The aim of this manuscript is to develop a one pot reaction for the synthesis of benzothiazole coupled pyrimidine compounds using alkynoic acids and substituted 2-aminobenzothiazoles under normal reaction conditions. Methods: Different 2-aminobenzothiazoles and substituted alkynoic acids have been used to synthesize 2H-Pyrimido[2,1-b]benzothiazol-2-ones via conjugate addition of the imino

  背景：在最近几年中，缩合嘧啶化合物因其巨大的生物学特性而备受关注。这些化合物引起了人们极大的兴趣，这在最近几年发表的大量评论和研究文章中得到了证明。该手稿的目的是开发一种在常规反应条件下使用炔酸和取代的2-氨基苯并噻唑合成一锅反应的方法，用于合成苯并噻唑偶联的嘧啶化合物。 方法：已使用不同的2-氨基苯并噻唑和取代的炔酸，通过将2-氨基苯并噻唑的亚氨基氮共轭加到炔酸的炔烃β-碳原子上来合成2H-嘧啶并[2,1-b]苯并噻唑-2-酮其次是闭环。根据元素分析和光谱数据（IR，1 H NMR，13 C NMR和质量）确定合成化合物的结构。评估合成的化合物的抗氧化剂（DPPH和ABTS分析）和抗菌活性（使用肉汤微量稀释法）。 结果：以中等至良好的产率（56-75％）获得了具有不同取代基的合成化合物。发现大多数化合物（6a，7a，8a）在DPPH和ABTS分析中具有更高的活性，并且还显示出显着的抗菌和抗真菌活性。