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An Efficient Synthesis and Reactions of 5-Acetyl-6-Methyl-4-(1,3-Diphenyl-1H-Pyrazol-4-yl)-3,4-Dihydropyrmidin-2(1H)-Thione as Potential Antimicrobial and Anti-Inflammatory Agents

Abstract

The synthesis of 5-acetyl-6-methyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-3,4-dihydropyrmidin-2(1H)-thione was achieved by one-pot three-component synthesis using CaCl2 in refluxing EtOH. The starting compound was utilized to synthesize a new series of 5-pyrazolyl; isoxazolyl; pyrimidinyl derivatives via the synthesized chalcone. Also, fused isoxazolo [5,4-d]pyrimidine and pyrazolo[3,4-d]pyrimidine were obtained by the treatment of 5-acetyl derivative with hydroxyl amine and/ or hydrazine hydrate. Also, the thiosemicarbazide derivative was prepared and utilized to synthesize other new thiazole derivatives. The structures of all compounds have been established on the basis of their analytical and spectral data. All compounds was also evaluated for their antibacterial and antifungal activity against various strains of bacteria and fungi. Also, the anti-inflammatory activity of some of synthesized compounds was evaluated using the carrageenan induced paw oedema test in rats using indomethacin as the reference drug.

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ACKNOWLEDGMENTS

The authors are grateful to Prof. Dr. Ahmed Moharem. professor of Botany and Microbiology department and the director of Mycology center and collogues of Faculty of Medicine, Assiut Univeristy for their kind help in performing the pharmacological screening.

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Correspondence to Shawkat A. Abdel-Mohsen.

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This article does not contain any studies involving human participants performed by any of the authors and does not contain any studies involving animals performed by any of the author.

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Talaat I. El-Emary, Abdel-Mohsen, S.A. & Mohamed, S.A. An Efficient Synthesis and Reactions of 5-Acetyl-6-Methyl-4-(1,3-Diphenyl-1H-Pyrazol-4-yl)-3,4-Dihydropyrmidin-2(1H)-Thione as Potential Antimicrobial and Anti-Inflammatory Agents. Russ J Bioorg Chem 47, 561–571 (2021). https://doi.org/10.1134/S1068162021020102

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  • DOI: https://doi.org/10.1134/S1068162021020102

Keywords:

  • one pot reaction
  • DHPMs
  • chalcone
  • azole
  • thiazole
  • biological activity