4-((5-acetyl-4-methylthiazol-2-yl)amino)benzonitrile | 1252426-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((5-acetyl-4-methylthiazol-2-yl)amino)benzonitrile
• 英文别名: 4-[(5-Acetyl-4-methyl-1,3-thiazol-2-yl)amino]benzonitrile
• CAS: 1252426-03-1
• 化学式: C₁₃H₁₁N₃OS
• 分子量: 257.316
• InChiKey: MZQXIWFPHWVSIS-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氰基苯硫脲 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 0.17h， 生成 4-((5-acetyl-4-methylthiazol-2-yl)amino)benzonitrile
  参考文献：
  名称：

  Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells

  摘要：

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.013

文献信息

• Iodine‐Mediated Three‐Component Strategy to Synthesize 2‐Aminothiazoles from β‐Diketones/β‐ketoesters, Arylamines and Ammonium Thiocyanate
  作者：Abigail Philips、Ajithkumar Arumugam、Yuvaprabhu Eswaramoorthy、Siva Senthil Kumar Boominathan、Gopal Chandru Senadi

  DOI：10.1002/ejoc.202201233

  日期：2022.12.12

  A one-pot, three-component protocol for the synthesis of 2-aminothiazoles promoted by iodine from readily available starting materials such as b-diketones/b-ketoesters, arylamines, and NH4SCN has been developed. A wide range of arylamines was tolerated well to produce the expected polysubstituted 2-aminothiazoles in moderate to good yields. The characteristic features of this methodology include operational

  已经开发了一种一锅三组分方案，用于从容易获得的起始材料（如 b-二酮/b-酮酯、芳基胺和 NH4SCN）合成 2-氨基噻唑。广泛的芳胺耐受性良好，以中等至良好的产率生产预期的多取代 2-氨基噻唑。该方法的特点包括操作简便、无金属反应条件、克级可扩展性、官能团耐受性和反应时间短。