1-(4-((4-(4-methoxyphenyl)thiazol-2-yl)amino)phenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-((4-(4-methoxyphenyl)thiazol-2-yl)amino)phenyl)ethanone
• 英文别名: 1-(4-{[4-(4-Methoxyphenyl)-1,3-thiazol-2-yl]amino}phenyl)ethanone；1-[4-[[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]amino]phenyl]ethanone
• 化学式: C₁₈H₁₆N₂O₂S
• 分子量: 324.403
• InChiKey: NVDLCDUSUUGZOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  盐酸氨基脲 、 1-(4-((4-(4-methoxyphenyl)thiazol-2-yl)amino)phenyl)ethanone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以70.8%的产率得到2-(1-(4-((4-(4-methoxyphenyl)thiazol-2-yl)amino)phenyl)ethylidene)hydrazinecarboxamide
  参考文献：
  名称：

  Evaluation of N-phenyl-2-aminothiazoles for treatment of multi-drug resistant and intracellular Staphylococcus aureus infections

  摘要：

  The increasing emergence of antibiotic-resistant bacterial pathogens calls for additional urgency in the development of new antibacterial candidates. N-Phenyl-2-aminothiazoles are promising candidates that possess potent anti-MRSA activity and could potentially replenish the MRSA antibiotic pipeline. The initial screen of a series of compounds in this novel class against several bacterial strains revealed that the aminoguanidine analogues possessed promising activities and superior safety profiles. The determined MICs of these compounds were comparable to, if not better than, those of the control drugs (linezolid and vancomycin). Remarkably, compounds 3a, 3b, and 3e possessed potent activities against multidrug resistant staphylococcal isolates and several clinically important pathogens, such as vancomycin-resistant enterococci (VRE) and Streptococcus pneumoniae. In addition, the compounds were superior to vancomycin in the rapid killing of MRSA and the longer post-antibiotic effects. Furthermore, low concentrations of compounds 3a, 3b, and 3e reduced the intracellular burden of MRSA by greater than 90%. Initial in vitro PK/toxicity assessments revealed that compound 3e was highly tolerable and possessed a low metabolic clearance rate and a highly acceptable half-life. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112497
• 作为产物：
  描述：

  4-氨基苯乙酮 在 盐酸 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 1-(4-((4-(4-methoxyphenyl)thiazol-2-yl)amino)phenyl)ethanone
  参考文献：
  名称：

  Evaluation of N-phenyl-2-aminothiazoles for treatment of multi-drug resistant and intracellular Staphylococcus aureus infections

  摘要：

  The increasing emergence of antibiotic-resistant bacterial pathogens calls for additional urgency in the development of new antibacterial candidates. N-Phenyl-2-aminothiazoles are promising candidates that possess potent anti-MRSA activity and could potentially replenish the MRSA antibiotic pipeline. The initial screen of a series of compounds in this novel class against several bacterial strains revealed that the aminoguanidine analogues possessed promising activities and superior safety profiles. The determined MICs of these compounds were comparable to, if not better than, those of the control drugs (linezolid and vancomycin). Remarkably, compounds 3a, 3b, and 3e possessed potent activities against multidrug resistant staphylococcal isolates and several clinically important pathogens, such as vancomycin-resistant enterococci (VRE) and Streptococcus pneumoniae. In addition, the compounds were superior to vancomycin in the rapid killing of MRSA and the longer post-antibiotic effects. Furthermore, low concentrations of compounds 3a, 3b, and 3e reduced the intracellular burden of MRSA by greater than 90%. Initial in vitro PK/toxicity assessments revealed that compound 3e was highly tolerable and possessed a low metabolic clearance rate and a highly acceptable half-life. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112497

文献信息

• Evaluation of N-phenyl-2-aminothiazoles for treatment of multi-drug resistant and intracellular Staphylococcus aureus infections
  作者：Inas G. Shahin、Nader S. Abutaleb、Marwa Alhashimi、Asmaa E. Kassab、Khaled O. Mohamed、Azza T. Taher、Mohamed N. Seleem、Abdelrahman S. Mayhoub

  DOI：10.1016/j.ejmech.2020.112497

  日期：2020.9

  The increasing emergence of antibiotic-resistant bacterial pathogens calls for additional urgency in the development of new antibacterial candidates. N-Phenyl-2-aminothiazoles are promising candidates that possess potent anti-MRSA activity and could potentially replenish the MRSA antibiotic pipeline. The initial screen of a series of compounds in this novel class against several bacterial strains revealed that the aminoguanidine analogues possessed promising activities and superior safety profiles. The determined MICs of these compounds were comparable to, if not better than, those of the control drugs (linezolid and vancomycin). Remarkably, compounds 3a, 3b, and 3e possessed potent activities against multidrug resistant staphylococcal isolates and several clinically important pathogens, such as vancomycin-resistant enterococci (VRE) and Streptococcus pneumoniae. In addition, the compounds were superior to vancomycin in the rapid killing of MRSA and the longer post-antibiotic effects. Furthermore, low concentrations of compounds 3a, 3b, and 3e reduced the intracellular burden of MRSA by greater than 90%. Initial in vitro PK/toxicity assessments revealed that compound 3e was highly tolerable and possessed a low metabolic clearance rate and a highly acceptable half-life. (C) 2020 Elsevier Masson SAS. All rights reserved.