4-phenyl-2-phenylamino-1,3-thiazole-5-carboxylic acid ethyl ether

• 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-phenyl-2-phenylamino-1,3-thiazole-5-carboxylic acid ethyl ether
• 英文别名: ethyl 4-phenyl-2-(phenylamino)thiazole-5-carboxylate；2-phenylamino-4-phenyl-5-ethoxycarbonylthiazole；5-ethoxycarbonyl-2-phenylamino-4-phenylthiazole；Ethyl 2-anilino-4-phenyl-1,3-thiazole-5-carboxylate
• 化学式: C₁₈H₁₆N₂O₂S
• 分子量: 324.403
• InChiKey: WPJDKZJWTYWGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Methyl benzimidate 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.0h， 生成 4-phenyl-2-phenylamino-1,3-thiazole-5-carboxylic acid ethyl ether
  参考文献：
  名称：

  One Pot Synthesis and Antimicrobial Activity of Substituted 2-Aminothiazoles

  摘要：

  在这项工作中，我们描述了通过两种不同的方法，使用一步法从甲氧基亚甲基-3-芳基-硫脲（2）开始制备取代的2-氨基噻唑。合成的2-氨基噻唑（5a-h）通过元素分析及其光谱（IR、1H NMR和13C NMR）数据进行表征，并评估了其生物活性。大多数化合物被发现具有显著的抗微生物活性。

  DOI：

  10.14233/ajchem.2015.19092

文献信息

• Reaction of Mercaptoacetate and Halides Containing Activated Methylenes with Thiocarbamoylimidates: A Novel Approach to the Synthesis of Aminothiazole Derivatives
  作者：K. Dridi、M. L. EL Efrit、B. Baccar、H. Zantour

  DOI：10.1080/00397919808005086

  日期：1998.1

  Abstract The reaction of N-thiocarbamoylimidates 1 with methyl thioglycolate leads to the formation of 4-arylamino-5-methoxycarbonylthiazoles 2. The condensation of the same imidates 1 on ethyl bromoacetate, benzyl bromide and chloroacetonitrile provides the corresponding 2-arylaminothiazoles 4.

  摘要 N-硫代氨基甲酰亚胺酯 1 与巯基乙酸甲酯反应生成 4-芳氨基-5-甲氧基羰基噻唑 2。相同的亚胺酯 1 在溴乙酸乙酯、苄基溴和氯乙腈上缩合得到相应的 2-芳基氨基噻唑 4。
• 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。
• Design, Synthesis, X-ray Crystallographic Analysis, and Biological Evaluation of Thiazole Derivatives as Potent and Selective Inhibitors of Human Dihydroorotate Dehydrogenase
  作者：Junsheng Zhu、Le Han、Yanyan Diao、Xiaoli Ren、Minghao Xu、Liuxin Xu、Shiliang Li、Qiang Li、Dong Dong、Jin Huang、Xiaofeng Liu、Zhenjiang Zhao、Rui Wang、Lili Zhu、Yufang Xu、Xuhong Qian、Honglin Li

  DOI：10.1021/jm501127s

  日期：2015.2.12

  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.
• Synthesis of 4-Substituted 2-Phenylaminothiazoles from Amidines. A Convenient Route to 4-Trichloromethylthiazoles
  作者：Moisés Romero-Ortega、Adriana Aviles、Raymundo Cruz、Aydee Fuentes、Rosa María Gómez、Andrés Plata

  DOI：10.1021/jo0009447

  日期：2000.10.1
• Reaction Of Mercaptoacetate and Halides Containing Activated Methylenes With Thioc Arb Amo Ylimidates: A Novel Approach To The Synthesis Of Aminothiazole Derivatives
  作者：K. Dridi、M. L. El Efrit、B. Baccar、H. Zantour

  DOI：10.1080/00397919908086191

  日期：1999.6

  The reaction of N-thiocarbamoylimidates (1) under bar with methyl thioglycolate leads to the formation of 4-arylamino-5-methoxycarbonylthiazoles (2) under bar. The condensation of the same imidates (1) under bar on ethyl bromoacetate, benzyl bromide and chloroacetonitrile provides the corresponding 2-arylaminothiazoles (4) under bar.