1-(2-((4-bromophenyl)amino)-4-methylthiazol-5-yl)ethanone | 112833-16-6

• 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-bromophenyl)amino)-4-methylthiazol-5-yl)ethanone
• 英文别名: 1-[2-(4-Bromoanilino)-4-methyl-1,3-thiazol-5-yl]ethanone
• CAS: 112833-16-6
• 化学式: C₁₂H₁₁BrN₂OS
• 分子量: 311.202
• InChiKey: OPNHBAJPHILCSX-UHFFFAOYSA-N

物化性质

• 沸点：
  424.9±55.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-((4-bromophenyl)amino)-4-methylthiazol-5-yl)ethanone 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 28.0h， 生成 (4-Bromo-phenyl)-[4-methyl-5-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-thiazol-2-yl]-amine
  参考文献：
  名称：

  Gawande, N. G.; Shingare, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 351 - 355

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯胺 在 ammonium hydroxide 、 三光气 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 4.17h， 生成 1-(2-((4-bromophenyl)amino)-4-methylthiazol-5-yl)ethanone
  参考文献：
  名称：

  Design, Synthesis, X-ray Crystallographic Analysis, and Biological Evaluation of Thiazole Derivatives as Potent and Selective Inhibitors of Human Dihydroorotate Dehydrogenase

  摘要：

  Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

  DOI：

  10.1021/jm501127s

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。
• GAWANDE, N. G.;SHINGARE, M. S., INDIAN J. CHEM., 26,(1987) N 4, 351-355
  作者：GAWANDE, N. G.、SHINGARE, M. S.

  DOI：——

  日期：——