2-(methylamino)-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one | 1396842-99-1

• 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: 2-(methylamino)-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
• 英文别名: 2-(Methylamino)-8-nitro-6-(trifluoromethyl)-1,3-benzothiazin-4-one；2-(methylamino)-8-nitro-6-(trifluoromethyl)-1,3-benzothiazin-4-one
• CAS: 1396842-99-1
• 化学式: C₁₀H₆F₃N₃O₃S
• 分子量: 305.237
• InChiKey: XYPALNNNRLLNRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(methylthio)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one 、 甲胺 以 乙醇 为溶剂， 以30.5%的产率得到2-(methylamino)-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
  参考文献：
  名称：

  Identification of Antitubercular Benzothiazinone Compounds by Ligand-Based Design

  摘要：

  1,3-Benzothiazin-4-ones (BTZs) are a novel class of TB drug candidates with potent activity against M. tuberculosis. An in silico ligand-based model based on structure-activity data from 170 BTZ compounds was used to design a new series. Compounds were tested against a panel of mycobacterial strains and were profiled for cytotoxicity, stability, and antiproliferative effects. Several of the compounds showed improved activity against MDR-TB while retaining low toxicity with higher microsomal, metabolic, and plasma stability.

  DOI：

  10.1021/jm3008882

文献信息

• Probes for rapid and specific detection of mycobacteria
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US10370538B2

  公开（公告）日：2019-08-06

  The compositions of the present disclosure provide novel fluorogenic probes for use in the specific imaging and detection of mycobacteria species, and in particular β-lactam-antibiotic resistant. Specificity for mycobacteria is conferred on these probes by incorporating a moiety that specifically targets the unique trapping mechanism of the DprE1 found in in mycobacteria. Accordingly, only Mycobacteria species that express both a β-lactamase and DprE1 enable both the activation of the caged fluorescent probe, and the affixing of the released fluorescent probes to the bacteria cells through the functioning reduction-covalent binding mechanism. Advantageously, such a probe is able, at its most sensitive, to allow single mycobacterium detection.

  本公开的组合物提供了新型荧光探针，可用于分枝杆菌，尤其是抗β-内酰胺类抗生素分枝杆菌的特异性成像和检测。这些探针加入了一个分子，专门针对分枝杆菌中 DprE1 的独特捕获机制，从而对分枝杆菌具有特异性。因此，只有同时表达 β-内酰胺酶和 DprE1 的分枝杆菌才能激活笼式荧光探针，并通过有效的还原-共价结合机制将释放的荧光探针粘附到细菌细胞上。更有利的是，这种探针的灵敏度最高，可用于单个分枝杆菌的检测。
• PROBES FOR RAPID AND SPECIFIC DETECTION OF MYCOBACTERIA
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20170044593A1

  公开（公告）日：2017-02-16

  The compositions of the present disclosure provide novel fluorogenic probes for use in the specific imaging and detection of mycobacteria species, and in particular β-lactam-antibiotic resistant. Specificity for mycobacteria is conferred on these probes by incorporating a moiety that specifically targets the unique trapping mechanism of the DprE1 found in in mycobacteria. Accordingly, only Mycobacteria species that express both a β-lactamase and DprE1 enable both the activation of the caged fluorescent probe, and the affixing of the released fluorescent probes to the bacteria cells through the functioning reduction-covalent binding mechanism. Advantageously, such a probe is able, at its most sensitive, to allow single mycobacterium detection.
• Identification of Antitubercular Benzothiazinone Compounds by Ligand-Based Design
  作者：Tomislav Karoli、Bernd Becker、Johannes Zuegg、Ute Möllmann、Soumya Ramu、Johnny X. Huang、Matthew A. Cooper

  DOI：10.1021/jm3008882

  日期：2012.9.13

  1,3-Benzothiazin-4-ones (BTZs) are a novel class of TB drug candidates with potent activity against M. tuberculosis. An in silico ligand-based model based on structure-activity data from 170 BTZ compounds was used to design a new series. Compounds were tested against a panel of mycobacterial strains and were profiled for cytotoxicity, stability, and antiproliferative effects. Several of the compounds showed improved activity against MDR-TB while retaining low toxicity with higher microsomal, metabolic, and plasma stability.