7-bromo-3-(ethylamino)benzo[e][1,2,4]triazine 1,4-dioxide | 1383844-90-3

• 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: 7-bromo-3-(ethylamino)benzo[e][1,2,4]triazine 1,4-dioxide
• 英文别名: 7-bromo-3-(ethylamino)benzo[e][1,2,4]triazine-1,4-dioxide；SRI-012464；7-bromo-N-ethyl-1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine
• CAS: 1383844-90-3
• 化学式: C₉H₉BrN₄O₂
• 分子量: 285.1
• InChiKey: PNSXWNNCUYDMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4'-溴乙酰苯胺 在 盐酸 、 双氧水 、 硝酸 、 乙酸酐 、 三乙胺 、 三氟乙酸 、 三氟乙酸酐 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 7-bromo-3-(ethylamino)benzo[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

文献信息

• Benzotriazine Oxides as Drugs Targeting Mycobacterium Tuberculosis
  申请人：Madrid Peter

  公开号：US20130150369A1

  公开（公告）日：2013-06-13

  Benzotriazine doxides are disclosed as drugs targeting mycobacterium tuberculosis , including novel compounds of formula I:

  Benzotriazine doxides被披露为针对结核分枝杆菌的药物，包括公式I的新化合物。
• BENZOTRIAZINE OXIDES AS DRUGS TARGETING MYCOBACTERIUM TUBERCULOSIS
  申请人：Sri International Inc.

  公开号：EP2800744A1

  公开（公告）日：2014-11-12
• US9663478B2
  申请人：——

  公开号：US9663478B2

  公开（公告）日：2017-05-30
• [EN] BENZOTRIAZINE OXIDES AS DRUGS TARGETING MYCOBACTERIUM TUBERCULOSIS<br/>[FR] OXYDES DE BENZOTRIAZINE EN TANT QUE MÉDICAMENTS CIBLANT MYCOBACTERIUM TUBERCULOSIS
  申请人：STANFORD RES INST INT

  公开号：WO2013086467A1

  公开（公告）日：2013-06-13

  Benzotriazine doxides are disclosed as drugs targeting mycobacterium tuberculosis, including novel compounds of formula I: (Formula (I)