1-[4-methyl-2-(4-nonylphenyl)thiazol-5-yl]ethanone | 1537168-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[4-methyl-2-(4-nonylphenyl)thiazol-5-yl]ethanone
• 英文别名: 1-[4-Methyl-2-(4-nonylphenyl)-1,3-thiazol-5-yl]ethanone；1-[4-methyl-2-(4-nonylphenyl)-1,3-thiazol-5-yl]ethanone
• CAS: 1537168-63-0
• 化学式: C₂₁H₂₉NOS
• 分子量: 343.533
• InChiKey: AIIIDXXXHIWRFI-UHFFFAOYSA-N

物化性质

• 沸点：
  474.4±47.0 °C(predicted)
• 密度：
  1.029±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-methyl-2-(4-nonylphenyl)thiazol-5-yl]ethanone 、 肼甲酰亚胺酰胺一氯化氢 在 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以55%的产率得到2-{1-[4-methyl-2-(4-nonylphenyl)thiazol-5-yl]ethylidene}hydrazinecarboximidamide
  参考文献：
  名称：

  Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant Staphylococcus aureus

  摘要：

  Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 mu g/mL.

  DOI：

  10.1021/jm401905m
• 作为产物：
  描述：

  4-nonylbenzamide 在 劳森试剂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 1-[4-methyl-2-(4-nonylphenyl)thiazol-5-yl]ethanone
  参考文献：
  名称：

  Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant Staphylococcus aureus

  摘要：

  Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 mu g/mL.

  DOI：

  10.1021/jm401905m

文献信息

• ANTIMICROBIAL SUBSTITUTED THIAZOLES AND METHODS OF USE
  申请人：Cushman Mark Stanley

  公开号：US20140121249A1

  公开（公告）日：2014-05-01

  Disclosed are compositions having activity against MRSA and/or VRSA, and methods of using the compositions to treat microbial infections.

  披露了对抗MRSA和/或VRSA活性的组合物，并使用这些组合物来治疗微生物感染的方法。
• US9353072B2
  申请人：——

  公开号：US9353072B2

  公开（公告）日：2016-05-31
• US9801861B2
  申请人：——

  公开号：US9801861B2

  公开（公告）日：2017-10-31
• Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant <i>Staphylococcus aureus</i>
  作者：Haroon Mohammad、Abdelrahman S. Mayhoub、Adil Ghafoor、Muhammad Soofi、Ruba A. Alajlouni、Mark Cushman、Mohamed N. Seleem

  DOI：10.1021/jm401905m

  日期：2014.2.27

  Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 mu g/mL.