1-(2-((4-fluorophenyl) amino)4-methylthiazol-5-yl)ethan-1-one | 952183-69-6

• 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-fluorophenyl) amino)4-methylthiazol-5-yl)ethan-1-one
• 英文别名: 1-[2-(4-Fluoroanilino)-4-methyl-1,3-thiazol-5-yl]-1-ethanone；1-[2-(4-fluoroanilino)-4-methyl-1,3-thiazol-5-yl]ethanone
• CAS: 952183-69-6
• 化学式: C₁₂H₁₁FN₂OS
• 分子量: 250.297
• InChiKey: NFQOLFFPQZMWSH-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167
• 沸点：
  381.4±52.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(2-((4-fluorophenyl) amino)4-methylthiazol-5-yl)ethan-1-one 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.07h， 以90%的产率得到(E)-2-(1-(2-((4-fluorophenyl)amino)-4-methylthiazol-5-yl)ethylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Thiazole fused thiosemicarbazones: Microwave-assisted synthesis, biological evaluation and molecular docking study

  摘要：

  In the present study, series of novel compounds (E)-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothio-amide (5a-j) and (E)-N-cyclohexyl-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothioamide (6a-j) have been synthesized using microwave irradiation method in high yields and characterized by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Synthesized compounds were evaluated for their in-vitro antimicrobial, antimalarial and anti-tuberculosis activity as well as in-silico study. The obtained results indicate that compound 6b and 6g were found to be the most potent against S. aureus bacterial strain. Further, the molecular docking study has been performed for all the new compounds with the immune system of S. aureus (PDB ID: 5D1Q) as a target enzyme, and this study validated the experimental results. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2018.11.025
• 作为产物：
  描述：

  4-氟苯胺 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-(2-((4-fluorophenyl) amino)4-methylthiazol-5-yl)ethan-1-one
  参考文献：
  名称：

  Fluorinated thiazole–thiosemicarbazones hybrids as potential PPAR-γ agonist and α-amylase, α-glucosidase antagonists: Design, synthesis, in silico ADMET and docking studies and hypoglycemic evaluation

  摘要：

  DOI：

  10.1016/j.molstruc.2023.137374

文献信息

• Visible Light-Mediated Coupling of Thioureas and 1,3-Dicarbonyls: Towards a Leaving Group-Free Synthesis of Aminothiazoles
  作者：Irwan Iskandar Roslan、Kian-Hong Ng、Mohammed Ashraf Gondal、Chanbasha Basheer、Mohamed A. Dastageer、Stephan Jaenicke、Gaik-Khuan Chuah

  DOI：10.1002/adsc.201701565

  日期：2018.4.17

  A synthesis of aminothiazoles from various 1,3‐dicarbonyls and thioureas without a leaving group has been developed. The reaction is photocatalyzed by tetraiodofluorescein, an organic dye. Under irradiation with green LEDs, a sulfur radical is generated in situ from thiourea, followed by addition to the enol tautomer, forming the aminothiazole backbone. This novel strategy provides a greener alternative

  已经开发了由各种1,3-二羰基和硫脲合成的不带离去基团的氨基噻唑的方法。该反应被有机染料四碘荧光素光催化。在绿色LED照射下，硫脲原位产生硫自由基，然后添加到烯醇互变异构体中，形成氨基噻唑骨架。这种新颖的策略提供了卓越的原子经济性，从而可以替代传统的离去基团方案，从而提供了更绿色的选择。
• 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。
• Thiazole fused thiosemicarbazones: Microwave-assisted synthesis, biological evaluation and molecular docking study
  作者：Neelam P. Prajapati、Kinjal D. Patel、Rajesh H. Vekariya、Hitesh D. Patel、Dhanaji P. Rajani

  DOI：10.1016/j.molstruc.2018.11.025

  日期：2019.3

  In the present study, series of novel compounds (E)-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothio-amide (5a-j) and (E)-N-cyclohexyl-2-(1-(4-methyl-2-(substituted-phenylamino)thiazol-5-yl)ethylidene)hydrazinecarbothioamide (6a-j) have been synthesized using microwave irradiation method in high yields and characterized by IR, H-1 NMR, C-13 NMR and mass spectral analysis. Synthesized compounds were evaluated for their in-vitro antimicrobial, antimalarial and anti-tuberculosis activity as well as in-silico study. The obtained results indicate that compound 6b and 6g were found to be the most potent against S. aureus bacterial strain. Further, the molecular docking study has been performed for all the new compounds with the immune system of S. aureus (PDB ID: 5D1Q) as a target enzyme, and this study validated the experimental results. (C) 2018 Elsevier B.V. All rights reserved.
• Fluorinated thiazole–thiosemicarbazones hybrids as potential PPAR-γ agonist and α-amylase, α-glucosidase antagonists: Design, synthesis, in silico ADMET and docking studies and hypoglycemic evaluation
  作者：Eman A. Fayed、Aya Thabet、Shimaa M. Abd El-Gilil、Heba M.A. Elsanhory、Yousry A. Ammar

  DOI：10.1016/j.molstruc.2023.137374

  日期：2024.4