3-hydroxy-5-methylbenzo[e][1,2,4]triazine-1-oxide | 27446-10-2

• 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-hydroxy-5-methylbenzo[e][1,2,4]triazine-1-oxide
• 英文别名: 5-methyl-1-oxy-4H-benzo[e][1,2,4]triazin-3-one；5-methyl-1-oxido-2H-1,2,4-benzotriazin-1-ium-3-one
• CAS: 27446-10-2
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: YNPVEAJXJDMQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-methylbenzo[e][1,2,4]triazine-1-oxide 在 双氧水 、 三乙胺 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(cyclopentylamino)-5-methylbenzo[e][1,2,4]triazine 1,4-dioxide
  参考文献：
  名称：

  Discovery and Optimization of Benzotriazine Di-N-Oxides Targeting Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Compounds bactericidal against both replicating and nonreplicating Mtb may shorten the length of TB treatment regimens by eliminating infections more rapidly. Screening of a panel of antimicrobial and anticancer drug classes that are bioreduced into cytotoxic species revealed that 1,2,4-benzotriazine di-N-oxides (BTOs) are potently bactericidal against replicating and nonreplicating Mtb. Medicinal chemistry optimization, guided by semiempirical molecular orbital calculations, identified a new lead compound (20q) from this series with an MIC of 0.31 mu g/mL against H37Rv and a cytotoxicity (CC50) against Vero cells of 25 mu g/mL. 20q also had equivalent potency against a panel of single-drug resistant strains of Mtb and remarkably selective activity for Mtb over a panel of other pathogenic bacterial strains. 20q was also negative in a L5178Y MOLY assay, indicating low potential for genetic toxicity. These data along with measurements of the physiochemical properties and pharmacokinetic profile demonstrate that BTOs have the potential to be developed into a new class of antitubercular drugs.

  DOI：

  10.1021/jm300123s
• 作为产物：
  描述：

  N-(2-甲基-6-硝基苯基)-乙酰胺 在 盐酸 、 三氟乙酸 、 sodium nitrite 作用下， 以 乙醚 、 水 为溶剂， 反应 8.0h， 生成 3-hydroxy-5-methylbenzo[e][1,2,4]triazine-1-oxide
  参考文献：
  名称：

  Discovery and Optimization of Benzotriazine Di-N-Oxides Targeting Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Compounds bactericidal against both replicating and nonreplicating Mtb may shorten the length of TB treatment regimens by eliminating infections more rapidly. Screening of a panel of antimicrobial and anticancer drug classes that are bioreduced into cytotoxic species revealed that 1,2,4-benzotriazine di-N-oxides (BTOs) are potently bactericidal against replicating and nonreplicating Mtb. Medicinal chemistry optimization, guided by semiempirical molecular orbital calculations, identified a new lead compound (20q) from this series with an MIC of 0.31 mu g/mL against H37Rv and a cytotoxicity (CC50) against Vero cells of 25 mu g/mL. 20q also had equivalent potency against a panel of single-drug resistant strains of Mtb and remarkably selective activity for Mtb over a panel of other pathogenic bacterial strains. 20q was also negative in a L5178Y MOLY assay, indicating low potential for genetic toxicity. These data along with measurements of the physiochemical properties and pharmacokinetic profile demonstrate that BTOs have the potential to be developed into a new class of antitubercular drugs.

  DOI：

  10.1021/jm300123s

文献信息

• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20190067600A1

  公开（公告）日：2019-02-28

  The present invention includes novel transition metal complexes with 1,2,4-triazine derivatives as ligands. The materials may be useful as emitter materials in organic electroluminescence device to improve the performance.

  本发明包括以1,2,4-三唑衍生物为配体的新型过渡金属配合物。这些材料可能用作有机电致发光器件中的发射材料，以提高性能。