5-{2-([1,1'-biphenyl]-4-yl)-4-methylthiazol-5-yl}-N-methyl-1,3,4-oxadiazol-2-amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-{2-([1,1'-biphenyl]-4-yl)-4-methylthiazol-5-yl}-N-methyl-1,3,4-oxadiazol-2-amine
• 英文别名: N-methyl-5-[4-methyl-2-(4-phenylphenyl)-1,3-thiazol-5-yl]-1,3,4-oxadiazol-2-amine
• 化学式: C₁₉H₁₆N₄OS
• 分子量: 348.428
• InChiKey: OSUOEFXJJZRTRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-联苯硫代甲酰胺 在 potassium carbonate 、 一水合肼 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-{2-([1,1'-biphenyl]-4-yl)-4-methylthiazol-5-yl}-N-methyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  Biphenylthiazole antibiotics with an oxadiazole linker: An approach to improve physicochemical properties and oral bioavailability

  摘要：

  A new series of oxadiazolylbiphenylthiazoles was prepared with the objective of improving the limited solubility of first-generation derivatives while maintaining antibacterial activity against drug-resistant Staphylococcus aureus. Studying the structure-activity relationship at the cationic part provided the piperazine-1-carboximidamide derivative 27 with a MIC (MRSA) value of 1.1 mu g/mL, bactericidal mode of action, and a 50-fold improvement in aqueous solubility. Additionally, 27 exhibited a wider safety margin against mammalian cells, and most importantly, a significant improvement in oral bioavailability. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.048

文献信息

• Biphenylthiazole antibiotics with an oxadiazole linker: An approach to improve physicochemical properties and oral bioavailability
  作者：Mohamed Hagras、Youssef A. Hegazy、Amr H. Elkabbany、Haroon Mohammad、Adel Ghiaty、Tamer M. Abdelghany、Mohamed N. Seleem、Abdelrahman S. Mayhoub

  DOI：10.1016/j.ejmech.2017.10.048

  日期：2018.1

  A new series of oxadiazolylbiphenylthiazoles was prepared with the objective of improving the limited solubility of first-generation derivatives while maintaining antibacterial activity against drug-resistant Staphylococcus aureus. Studying the structure-activity relationship at the cationic part provided the piperazine-1-carboximidamide derivative 27 with a MIC (MRSA) value of 1.1 mu g/mL, bactericidal mode of action, and a 50-fold improvement in aqueous solubility. Additionally, 27 exhibited a wider safety margin against mammalian cells, and most importantly, a significant improvement in oral bioavailability. (C) 2017 Elsevier Masson SAS. All rights reserved.