4-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2H-benzo[b][1,4]thiazin-3(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2H-benzo[b][1,4]thiazin-3(4H)-one
• 英文别名: 4-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-2H-1,4-benzothiazin-3(4H)-one；4-[(1-Benzyltriazol-4-yl)methyl]-1,4-benzothiazin-3-one；4-[(1-benzyltriazol-4-yl)methyl]-1,4-benzothiazin-3-one
• 化学式: C₁₈H₁₆N₄OS
• 分子量: 336.417
• InChiKey: VJOZKTYJYFQYHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2H)1,4-苯并噻嗪-3(4H)-酮 在 copper diacetate 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 28.0h， 生成 4-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2H-benzo[b][1,4]thiazin-3(4H)-one
  参考文献：
  名称：

  Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent

  摘要：

  In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 mu g/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 mu g/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.071

文献信息

• Novel 1,4-benzothiazine derivatives: synthesis, crystal structure, and anti-bacterial properties
  作者：Nada Kheira Sebbar、Mohamed El Mehdi Mekhzoum、El Mokhtar Essassi、Abdelfettah Zerzouf、Ahmed Talbaoui、Youssef Bakri、Mohamed Saadi、Lahcen El Ammari

  DOI：10.1007/s11164-016-2499-6

  日期：2016.9

  4-benzothiazi-3-one in good yields. The crystal and molecular structure of compound oxazolidin-2-one in basic benzothiazine was established by single-crystal X-ray diffraction. The newly synthesized products were subjected to in vitro biological evaluation. The result indicated that the compounds show convincing antibacterial activities against different microorganisms. All structures of the synthesized compounds

  为了开发相对小的分子作为药理活性分子，合成了具有三唑和恶唑烷酮的新型1，4-苯并噻嗪衍生物。在这项研究中，通过利用CuI催化的Huisgen [3 + 2]环加成反应的点击化学反应，开发了一系列1,2,3-三唑基甲基-1,4-苯并噻嗪衍生物。从2-（取代的）-3,4-二氢-2H-1,4-苯并噻唑-3-一开始，还使用不同的烷基化剂合成了许多1,4-苯并噻嗪衍生物以得到4-（取代的） -2-（取代的）-3,4-二氢-2H-1,4-苯并噻唑-3-酮具有良好的收率。通过单晶X射线衍射建立了碱性苯并噻嗪中恶唑烷-2-酮化合物的晶体和分子结构。对新合成的产物进行体外生物学评估。结果表明这些化合物对不同的微生物显示出令人信服的抗菌活性。在光谱分析和化学反应的基础上阐明了合成化合物的所有结构。
• Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent
  作者：Mubarak H. Shaikh、Dnyaneshwar D. Subhedar、Manisha Arkile、Vijay M. Khedkar、Nandadeep Jadhav、Dhiman Sarkar、Bapurao B. Shingate

  DOI：10.1016/j.bmcl.2015.11.071

  日期：2016.1

  In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 mu g/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 mu g/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents. (C) 2015 Elsevier Ltd. All rights reserved.