1-{2-[4-(tert-butyl)phenyl]-4-methylthiazol-5-yl}ethanone | 1268085-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{2-[4-(tert-butyl)phenyl]-4-methylthiazol-5-yl}ethanone
• 英文别名: 1-[2-(4-Tert-butylphenyl)-4-methyl-1,3-thiazol-5-yl]ethanone
• CAS: 1268085-01-3
• 化学式: C₁₆H₁₉NOS
• mdl: MFCD13498575
• 分子量: 273.399
• InChiKey: JAGRQYQMXXPNBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 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-{2-[4-(tert-butyl)phenyl]-4-methylthiazol-5-yl}ethanone 在 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 34.0h， 生成 1-(4-(2-(4-(tert-butyl)phenyl)-4-methylthiazol-5-yl)pyrimidin-2-yl)-3-methylguanidine
  参考文献：
  名称：

  Phenylthiazoles with tert-Butyl side chain: Metabolically stable with anti-biofilm activity

  摘要：

  A new series of phenylthiazoles with t-butyl lipophilic component was synthesized and their antibacterial activity against a panel of multidrug-resistant bacterial pathogens was evaluated. Five compounds demonstrated promising antibacterial activity against methicillin-resistant staphylococcal strains and several vancomycin-resistant staphylococcal and enterococcal species. Additionally, three derivatives 19, 23 and 26 exhibited rapid bactericidal activity, and remarkable ability to disrupt mature biofilm produced by MRSA USA300. More importantly, a resistant mutant to 19 couldn't be isolated after subjecting MRSA to sub-lethal doses for 14 days. Lastly, this new series of phenylthiazoles possesses an advantageous attribute over the first-generation compounds in their stability to hepatic metabolism, with a biological half-life of more than 9 h. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.03.044
• 作为产物：
  描述：

  对叔丁基苯甲酰氯 在 劳森试剂 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 1-{2-[4-(tert-butyl)phenyl]-4-methylthiazol-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

• PHENYLTHIAZOLES AND USES THEREOF
  申请人：Purdue Research Foundation

  公开号：US20180319784A1

  公开（公告）日：2018-11-08

  Series of 2-phenyl-4-methylthiazole analogues are disclosed as potential therapeutic agents for the treatment of bacterial infections, especially methicillin-resistant Straphylococcus aureus (MRSA) related infections. A method for the treatment of MRSA-related infections is also claimed.

  一系列2-苯基-4-甲基噻唑类似物被披露为治疗细菌感染，特别是耐甲氧西林金黄色葡萄球菌（MRSA）相关感染的潜在治疗药物。还声明了一种治疗MRSA相关感染的方法。
• 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。
• Novel phenylthiazoles with a <i>tert</i>-butyl moiety: promising antimicrobial activity against multidrug-resistant pathogens with enhanced ADME properties
  作者：Mohamed Hagras、Abdelrahman A. Abuelkhir、Nader S. Abutaleb、Ahmed M. Helal、Iten M. Fawzy、Maghawry Hegazy、Mohamed N. Seleem、Abdelrahman S. Mayhoub

  DOI：10.1039/d3ra07619a

  日期：——

  concentration (MIC) of 4 μg mL-1. One of these two compounds demonstrated potent activity against C. difficile, with a MIC of 4 μg mL-1. Moderate activities against a C. difficile strain with a MIC of 8 μg mL-1 were noted. Some new compounds possessed antifungal activity against a wild fluconazole-resistant C. albicans strain, with MIC values of 4-16 μg mL-1. ADME and metabolism-simulation studies were

  研究了带有嘧啶连接体的新型叔丁基苯基噻唑系列的构效关系。我们希望通过生成 21 种侧链含有 ≥2 个杂原子的新衍生物来扩展对此类新型抗生素的了解。检测了它们对耐甲氧西林金黄色葡萄球菌 (MRSA)、艰难梭菌、大肠杆菌、淋病奈瑟菌和白色念珠菌分离株的活性。两种以 1,2-二氨基环己烷作为含氮侧链的化合物对高传染性 MRSA USA300 菌株表现出良好的活性，最低抑制浓度 (MIC) 为 4 μg mL-1。这两种化合物中的一种对艰难梭菌具有有效的活性，MIC 为 4 μg mL-1。注意到对艰难梭菌菌株具有中等活性，MIC 为 8 μg mL-1。一些新化合物对野生氟康唑耐药白色念珠菌菌株具有抗真菌活性，MIC值为4-16 μg mL-1。对最有前途的化合物进行了 ADME 和代谢模拟研究，并与先导化合物进行了比较。我们的结果表明，一种化合物具有更强的细菌膜渗透性和代谢抵抗力，这有助于延长针对
• Phenylthiazoles and uses thereof
  申请人：Purdue Research Foundation

  公开号：US10414759B2

  公开（公告）日：2019-09-17

  Series of 2-phenyl-4-methylthiazole analogs are disclosed as potential therapeutic agents for the treatment of bacterial infections, especially methicillin-resistant Straphylococcus aureus (MRSA) related infections. A method for the treatment of MRSA-related infections is also claimed.

  本发明公开了一系列 2-苯基-4-甲基噻唑类似物，它们是治疗细菌感染，特别是耐甲氧西林金黄色葡萄球菌（MRSA）相关感染的潜在治疗剂。还提出了一种治疗 MRSA 相关感染的方法。
• US9353072B2
  申请人：——

  公开号：US9353072B2

  公开（公告）日：2016-05-31