2-(4-isobutoxyphenyl)-4-methy-5-acetylthiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-isobutoxyphenyl)-4-methy-5-acetylthiazole
• 英文别名: 1-[4-Methyl-2-[4-(2-methylpropoxy)phenyl]-1,3-thiazol-5-yl]ethanone；1-[4-methyl-2-[4-(2-methylpropoxy)phenyl]-1,3-thiazol-5-yl]ethanone
• 化学式: C₁₆H₁₉NO₂S
• 分子量: 289.398
• InChiKey: KDJCKFDRWBCPFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-isobutoxyphenyl)-4-methy-5-acetylthiazole 、 肼甲酰亚胺酰胺一氯化氢 在 potassium carbonate 、 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以80%的产率得到2-(1-(2-(4-isobutoxyphenyl)-4-methylthiazol-5-yl)ethylidene)hydrazine-1-carboximidamide
  参考文献：
  名称：

  Phenylthiazole antibiotics: A metabolism-guided approach to overcome short duration of action

  摘要：

  Antibacterial resistance is a pressing global health challenge that necessitates the development of new therapeutic agents. Phenylthiazole antibacterial agents have been extensively studied, by our group, as a potential novel class of antibiotics to circumvent the scourge of antibacterial resistance. Previously, the phenylthiazole lead compound I was shown to possess potent activity against clinical isolates of methicillin-and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA). The promising activity of this novel class of antibiotics is hampered by their short half-life due to rapid hepatic metabolism. In the present study, a metabolic methylene soft spot in the lead 1 was identified and replaced with an oxygen atom. The newly developed phenylthiazoles, with alkoxy side chains, demonstrate high metabolic stability (t(1/2) > 4 h), while maintaining their potent anti-MRSA activity. Furthermore, compound 5p demonstrated a selective advantage over vancomycin with its ability to kill intracellular MRSA.(C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.042
• 作为产物：
  描述：

  4-羟基硫代苯甲酰胺 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(4-isobutoxyphenyl)-4-methy-5-acetylthiazole
  参考文献：
  名称：

  Phenylthiazole antibiotics: A metabolism-guided approach to overcome short duration of action

  摘要：

  Antibacterial resistance is a pressing global health challenge that necessitates the development of new therapeutic agents. Phenylthiazole antibacterial agents have been extensively studied, by our group, as a potential novel class of antibiotics to circumvent the scourge of antibacterial resistance. Previously, the phenylthiazole lead compound I was shown to possess potent activity against clinical isolates of methicillin-and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA). The promising activity of this novel class of antibiotics is hampered by their short half-life due to rapid hepatic metabolism. In the present study, a metabolic methylene soft spot in the lead 1 was identified and replaced with an oxygen atom. The newly developed phenylthiazoles, with alkoxy side chains, demonstrate high metabolic stability (t(1/2) > 4 h), while maintaining their potent anti-MRSA activity. Furthermore, compound 5p demonstrated a selective advantage over vancomycin with its ability to kill intracellular MRSA.(C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.11.042