3-N-(4-fluorophenyl)-4,5-tetramethylene thieno-[2,3-d][1,2,3]-triazin-4(3H)-one | 1246527-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-N-(4-fluorophenyl)-4,5-tetramethylene thieno-[2,3-d][1,2,3]-triazin-4(3H)-one
• 英文别名: 3-(4-fluorophenyl)tetrahydrobenzo[b]thieno[2,3-d][1,2,3]triazin-4(3H)-one；3-(4-Fluorophenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]triazin-4-one
• CAS: 1246527-90-1
• 化学式: C₁₅H₁₂FN₃OS
• 分子量: 301.344
• InChiKey: SLRWKEFHAZFTPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (4-fluorophenyl)amide 在 盐酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 以67%的产率得到3-N-(4-fluorophenyl)-4,5-tetramethylene thieno-[2,3-d][1,2,3]-triazin-4(3H)-one
  参考文献：
  名称：

  Synthesis of some 3-substituted amino-4,5-tetramethylene thieno[2,3-d][ 1,2,3]-triazin-4(3H)-ones as potential antimicrobial agents

  摘要：

  A series of 3-Substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3 (H) under bar )ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activity by agar diffusion method against four bacteria and three fungi using Ampicillin and Miconazole nitrate as standards. The compounds Villa, IXa, Xa and XIa showed an antimicrobial efficacy considerably greater than the compounds la to Vila with -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substitutions at R. suggesting that lipophillic groups like chloro, fluoro substitution on the phenyl ring plays an important role in enhancing the antimicrobial properties of this class of compounds.From the screening results it can be concluded that the compounds having the lipophillic groups like chlorophenyl and fluorophenyl groups at R exhibited appreciable antimicrobial activities. Whereas, the compounds are having -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substituents at R were less active against all the organisms used. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.061

文献信息

• Cu-mediated N-arylation of 1,2,3-triazin-4-ones: Synthesis of fused triazinone derivatives as potential inhibitors of chorismate mutase
  作者：K. Shiva Kumar、Raju Adepu、Sandhya Sandra、D. Rambabu、G. Rama Krishna、C. Malla Reddy、Parimal Misra、Manojit Pal

  DOI：10.1016/j.bmcl.2011.11.096

  日期：2012.1

  methodology. Molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. The scope and limitations of this reaction is discussed. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro. The in vitro dose response study of an active compound is presented.

  通过1,2,3-三嗪-4-酮环的N-芳基化，涉及三嗪酮衍生物与芳基硼酸之间的铜介导偶联，可以快速，直接地获得N-芳基取代的稠合三嗪酮衍生物。发现Cu（OAc）2 -Et 3 N在1,2-二氯乙烷中的组合是有效的，并且使用此方法已制备了各种稠合的三嗪酮衍生物。通过单晶X射线衍射研究证实了代表性化合物的分子结构。讨论了该反应的范围和局限性。在体外测试了一些合成的化合物的分支酸突变酶抑制特性。提出了活性化合物的体外剂量反应研究。
• Synthesis of some 3-substituted amino-4,5-tetramethylene thieno[2,3-d][ 1,2,3]-triazin-4(3H)-ones as potential antimicrobial agents
  作者：Janardhanan Saravanan、Shamanna Mohan、Jay Jyoti Roy

  DOI：10.1016/j.ejmech.2010.05.061

  日期：2010.9

  A series of 3-Substituted amino-4,5-tetramethylene thieno[2,3-d] [1,2,3]-triazine-4(3 (H) under bar )ones have been synthesized and characterized by UV,IR, 1H NMR, elemental and mass spectral analysis. The title compounds were evaluated for their antimicrobial activity by agar diffusion method against four bacteria and three fungi using Ampicillin and Miconazole nitrate as standards. The compounds Villa, IXa, Xa and XIa showed an antimicrobial efficacy considerably greater than the compounds la to Vila with -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substitutions at R. suggesting that lipophillic groups like chloro, fluoro substitution on the phenyl ring plays an important role in enhancing the antimicrobial properties of this class of compounds.From the screening results it can be concluded that the compounds having the lipophillic groups like chlorophenyl and fluorophenyl groups at R exhibited appreciable antimicrobial activities. Whereas, the compounds are having -H, phenyl and electron donating (activating) groups like methyl, ethyl and tolyl substituents at R were less active against all the organisms used. (C) 2010 Elsevier Masson SAS. All rights reserved.