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Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts

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Abstract

In the present study, synthesis of a variety of 5-bromo-4-methyl-2-substituted pyrimidines endowed with pyrazolyl substituent appended in C4 position (7a-f) is described. These products are generated via treatment of 5-bromo-4-hydrazineyl-6-methyl-2-substituted pyrimidines (6a–f) and vinamidinum salt of (E)-N-(3-(dimethylamino)-2-phenylallylidene)-N-methylmethanaminium perchlorate (5) in good to excellent yields. The inhibitory and hydrogen-atom donating abilities of the synthesized products (7a-f) were assessed against nine pathogens including six bacterial strains (both Gram-negative and Gram-positive), three fungal strains and DPPH free radicals. Notable antioxidant properties were not observed with the products. IC50 values were in the range of 107.49–929.16 μg ml−1. The inhibition zone diameters of products at 10 mg ml−1 concentrations were recorded in the range of 10.51–18.44 mm via disk diffusion method. 5-Bromo-4-methyl-6-pyrazolylpyrimidine (7e) containing 2-(4-methylpiperazin) substituent showed better antioxidant and antimicrobial effects than other products. It was effective on all the tested microbial strains except Staphylococcus epidermidis. All the synthesized pyrazolyl pyrimidines, especially (7e) can be used to disinfect the environment and treat infectious diseases.

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Acknowledgements

The authors gratefully acknowledge the Research Council of Ferdowsi University of Mashhad for financial support of this project (3/56454).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Roya Maghamifar, Seddigheh Sheikhi-Mohammareh & Ali Shiri

  2. Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

    Hamid Beyzaei

  3. Department of Biology, Faculty of Science, University of Zabol, Zabol, Iran

    Zahra Ebrahimnezhad

Authors
  1. Roya Maghamifar
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  2. Seddigheh Sheikhi-Mohammareh
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  3. Hamid Beyzaei
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  4. Zahra Ebrahimnezhad
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  5. Ali Shiri
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Correspondence to Ali Shiri.

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Maghamifar, R., Sheikhi-Mohammareh, S., Beyzaei, H. et al. Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts. J IRAN CHEM SOC 20, 2297–2305 (2023). https://doi.org/10.1007/s13738-023-02837-3

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  • DOI: https://doi.org/10.1007/s13738-023-02837-3

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