1-(2-(4-butylphenyl)-4-methylthiazol-5-yl)ethanone | 1313711-81-7

• 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-(2-(4-butylphenyl)-4-methylthiazol-5-yl)ethanone
• 英文别名: 1-[2-(4-Butylphenyl)-4-methyl-1,3-thiazol-5-yl]ethanone
• CAS: 1313711-81-7
• 化学式: C₁₆H₁₉NOS
• 分子量: 273.399
• InChiKey: PZLAEDBOESDYLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.1±47.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 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：
  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-butylphenyl)-4-methylthiazol-5-yl)ethanone 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 5-([1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-2-(4-butylphenyl)-4-methylthiazole
  参考文献：
  名称：

  具有增强的药代动力学特性的第二代苯基噻唑抗生素

  摘要：

  合成了一系列第二代2-（1-（2-（4-丁基苯基）-4-甲基噻唑-5-基）亚乙基）氨基胍（1）的类似物，并针对耐甲氧西林的金黄色葡萄球菌（MRSA）进行了测试。 。设计这些化合物的目的是改善药代动力学性质。通过用环状的不可水解的嘧啶环取代第一代成员的可快速水解的席夫碱部分来实现该主要目的。含酰肼的类似物17被确定为迄今为止构建的最有效的类似物。相应的胺8活跃度降低了8倍。最后，将含氮侧链并入芳族体系中完全消除了抗菌特性。用环状生物等排体取代正丁基可显示出环己烯基类似物29，该化合物在体外抗MRSA效能方面表现出显着改善。增大或减小环的尺寸会使抗菌活性变差。化合物17表现出优异的体外和体内药代动力学特性，提供了令人信服的证据证明这种特定的类似物是值得进一步分析的良好候选药物。

  DOI：

  10.1021/acs.jmedchem.6b00233
• 作为产物：
  描述：

  4-丁基苯甲酰胺 在 劳森试剂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 1-(2-(4-butylphenyl)-4-methylthiazol-5-yl)ethanone
  参考文献：
  名称：

  ANTIMICROBIAL SUBSTITUTED THIAZOLES AND METHODS OF USE

  摘要：

  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。

  公开号：

  US20140121249A1

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。
• 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.
• An investigation of phenylthiazole antiflaviviral agents
  作者：Abdelrahman S. Mayhoub、Mansoora Khaliq、Carolyn Botting、Ze Li、Richard J. Kuhn、Mark Cushman

  DOI：10.1016/j.bmc.2011.04.041

  日期：2011.6

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.
• Arylthiazole antibiotics targeting intracellular methicillin-resistant Staphylococcus aureus (MRSA) that interfere with bacterial cell wall synthesis
  作者：Islam Eid、Mohamed M. Elsebaei、Haroon Mohammad、Mohamed Hagras、Christine E. Peters、Youssef A. Hegazy、Bruce Cooper、Joe Pogliano、Kit Pogliano、Hamada S. Abulkhair、Mohamed N. Seleem、Abdelrahman S. Mayhoub

  DOI：10.1016/j.ejmech.2017.08.039

  日期：2017.10

  The promising antibacterial potency of arylthiazole antibiotics is offset by their limited activity against intracellular bacteria (namely methicillin-resistant Staphylococcus aureus (MRSA)), similar to many clinically-approved antibiotics. The failure to target these hidden pathogens is due to the compounds' lack of proper characteristics to accumulate intracellularly. Fine tuning of the size and polar-surface-area of the linking heteroaromatic ring provided a new series of 5-thiazolylarylthiazoles with balanced properties that allow them to sufficiently cross and accumulate inside macrophages infected with MRSA. The most promising compound 4i exhibited rapid bactericidal activity, good metabolic stability and produced over 80% reduction of intracellular MRSA in infected macrophages. (C) 2017 Elsevier Masson SAS. All rights reserved.
• US9801861B2
  申请人：——

  公开号：US9801861B2

  公开（公告）日：2017-10-31