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Study on Condensation of N-Aryl Thioureas with 3-Bromo-acetylacetone: Synthesis of Aminothiazoles and Iminodihydrothiazoles, and Their In Vitro Antiproliferative Activity on Human Cervical Cancer Cells

  作者 SHI HAIBO; ZHANG SHIJIE; LIN YANFANG; HU WEIXIAO; CAI CHAOMING  
  选自 期刊  Journal of Heterocyclic Chemistry;  卷期  2011年48-5;  页码  1061-1066  
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[摘要]The condensation of N-aryl thioureas with 3-bromo-acetylacetone in neutral solvent acetone not only led to 5-acetyl-4-methyl-2-(substituted anilino) thiazoles 3 but also 2-imino-3-(substituted phenyl)-4-methyl-5-acetyl-2,3-dihydrothiazoles 4. Further study found that different reaction solvents displayed an important role toward the ratio of aminothiazoles 3 and iminodihydrothiazoles 4, and the reaction scope was extended. A plausible mechanism involving solvent effect and in situ hydrobromic acid catalyzation was proposed. Some selected isomers exhibited moderate in vitro antiproliferative activity on human cervical cancer cell lines (Hela, Siha).

 
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