2-(4-ethyloxyphenyl)-4-methy-5-acetylthiazole | 71633-86-8

• 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-ethyloxyphenyl)-4-methy-5-acetylthiazole
• 英文别名: 5-Acetyl-2(4-ethoxyphenyl)-4-methyl-1,3-thiazol；1-[2-(4-ethoxy-phenyl)-4-methyl-thiazol-5-yl]-ethanone；Ethanone, 1-[2-(4-ethoxyphenyl)-4-methyl-5-thiazolyl]-；1-[2-(4-ethoxyphenyl)-4-methyl-1,3-thiazol-5-yl]ethanone
• CAS: 71633-86-8
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD13223976
• 分子量: 261.345
• InChiKey: SNWYTRSEDYSEAB-UHFFFAOYSA-N

物化性质

• 沸点：
  412.5±55.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 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-ethyloxyphenyl)-4-methy-5-acetylthiazole 在 potassium dichromate 、 氢氧化钾 、 selenium(IV) oxide 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 27.0h， 生成 2-(4-ethoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid
  参考文献：
  名称：

  Heterocyclen, 53rd Mitt. 2-aryl-4-R-5-glyoxyloyl-thiazoles 的合成和抗菌作用

  摘要：

  描述了通过氧化相应的 5-乙酰基-噻唑制备 2-芳基-4-R-5-乙醛酰-噻唑、它们的化学特征和它们的抗菌作用。

  DOI：

  10.1002/ardp.19813140904
• 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-ethyloxyphenyl)-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

文献信息

• SIMITI, I.;MURESAN, A.;COMAN, M., ARCH. PHARM., 1981, 314, N 9, 744-750
  作者：SIMITI, I.、MURESAN, A.、COMAN, M.

  DOI：——

  日期：——