methanesulfonic acid 2-(2-{[5-(2,6-dichlorophenyl)[1,2,4]-triazin-3-ylamino]methyl}benzothiazol-5-yloxy)ethyl ester | 1426097-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: methanesulfonic acid 2-(2-{[5-(2,6-dichlorophenyl)[1,2,4]-triazin-3-ylamino]methyl}benzothiazol-5-yloxy)ethyl ester
• 英文别名: 2-[[2-[[[5-(2,6-Dichlorophenyl)-1,2,4-triazin-3-yl]amino]methyl]-1,3-benzothiazol-5-yl]oxy]ethyl methanesulfonate；2-[[2-[[[5-(2,6-dichlorophenyl)-1,2,4-triazin-3-yl]amino]methyl]-1,3-benzothiazol-5-yl]oxy]ethyl methanesulfonate
• CAS: 1426097-21-3
• 化学式: C₂₀H₁₇Cl₂N₅O₄S₂
• 分子量: 526.424
• InChiKey: MUVMQBLXLRBBKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 2-(2-{[5-(2,6-dichlorophenyl)[1,2,4]-triazin-3-ylamino]methyl}benzothiazol-5-yloxy)ethyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.0h， 生成 N'-(3-aminopropyl)-N'-[2-[[2-[[[5-(2,6-dichlorophenyl)-1,2,4-triazin-3-yl]amino]methyl]-1,3-benzothiazol-5-yl]oxy]ethyl]propane-1,3-diamine
  参考文献：
  名称：

  Vectorization Efforts To Increase Gram-Negative Intracellular Drug Concentration: A Case Study on HldE-K Inhibitors

  摘要：

  In this paper, we present different strategies to vectorize HldE kinase inhibitors with the goal to improve their Gram-negative intracellular concentration. Syntheses and biological effects of siderophoric, aminoglycosidic, amphoteric, and polycationic vectors are discussed. While siderophoric and amphoteric vectorization efforts proved to be disappointing in this series, aminoglycosidic and polycationic vectors were able for the first time to achieve synergistic effects of our inhibitors with erythromycin. Although these effects proved to be nonspecific, this study provides information about the required stereoelectronic arrangement of the polycationic amines and their basicity requirements to fulfill outer membrane destabilization resulting in better erythromycin synergies.

  DOI：

  10.1021/jm400097h
• 作为产物：
  描述：

  2-(2-{[5-(2,6-dichlorophenyl)[1,2,4]triazin-3-ylamino]methyl}benzothiazol-5-yloxy)ethanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 methanesulfonic acid 2-(2-{[5-(2,6-dichlorophenyl)[1,2,4]-triazin-3-ylamino]methyl}benzothiazol-5-yloxy)ethyl ester
  参考文献：
  名称：

  Vectorization Efforts To Increase Gram-Negative Intracellular Drug Concentration: A Case Study on HldE-K Inhibitors

  摘要：

  In this paper, we present different strategies to vectorize HldE kinase inhibitors with the goal to improve their Gram-negative intracellular concentration. Syntheses and biological effects of siderophoric, aminoglycosidic, amphoteric, and polycationic vectors are discussed. While siderophoric and amphoteric vectorization efforts proved to be disappointing in this series, aminoglycosidic and polycationic vectors were able for the first time to achieve synergistic effects of our inhibitors with erythromycin. Although these effects proved to be nonspecific, this study provides information about the required stereoelectronic arrangement of the polycationic amines and their basicity requirements to fulfill outer membrane destabilization resulting in better erythromycin synergies.

  DOI：

  10.1021/jm400097h