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Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

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Abstract

Pyrazolo[3,4-d]pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gram-negative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32–4096 μg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.

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Acknowledgements

The authors would like to thank members of the University of Zabol especially Dr Mohammad Allahbakhsh, Deputy of Research and Technology, and Dr Mansour Ghaffari-Moghaddam, Dean of the Faculty of Science, for their support and assistance at the various stages of this project.

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  1. Hamid Beyzaei

    Present address: Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

Authors and Affiliations

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

    Reza Aryan & Alireza Samzadeh-Kermani

  2. Department of Chemistry, Faculty of Science, Kerman Branch, Islamic Azad University, Kerman, Iran

    Mohammadreza Moghaddam-Manesh

  3. Young Researchers and Elite Club, Neyshabur Branch, Islamic Azad University, Neyshabur, Iran

    Behzad Ghasemi

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  1. Hamid Beyzaei
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  2. Mohammadreza Moghaddam-Manesh
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  4. Behzad Ghasemi
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Correspondence to Hamid Beyzaei.

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Beyzaei, H., Moghaddam-Manesh, M., Aryan, R. et al. Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines. Chem. Pap. 71, 1685–1691 (2017). https://doi.org/10.1007/s11696-017-0163-2

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