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Medicinal Chemistry Research

, Volume 26, Issue 11, pp 2909–2919 | Cite as

Synthesis and biological evaluation of pyrazolo[1,5-a]pyrimidine-3-carboxamide as antimicrobial agents

  • Ashraf S. Hassan
  • Doaa M. Masoud
  • Farid M. Sroor
  • Ahmed A. Askar
Original Research

Abstract

Exploring novel classes of antimicrobial therapeutics is an excellent approach to face the challenge of microbial resistance. In this context, a novel series of pyrazolo[1,5-a]pyrimidines 5ad, 10af, 15a, d and 16ad were synthesized and characterized by their spectral data. The structure of 10f was confirmed by X-ray diffraction analysis of its single crystal. The antimicrobial activities of the newly synthesized compounds showed that, compounds 5a and 16d were more potent than tetracycline against Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli. In addition, most of the newly synthesized compounds displayed a significant antifungal activity when compared with amphotericin B. Moreover, compound 16d (27.0 ± 0.41 mm, minimum inhibitory concentration: 7.81 µg/ml) displayed excellent and the highest antifungal activity than amphotericin B (18.0 ± 0.17 mm, MIC: 15.62 µg/ml) against Fusarium oxysporum.

Keywords

5-Aminopyrazole Pyrazolo[1,5-a]pyrimidine Antimicrobial agents X-ray crystallography 

Notes

Acknowledgements

The authors wish to express their thanks to the National Research Centre for the facilities provided. Farid Sroor is grateful to the embassy of France in Cairo for a postdoctoral scholarship within the Institut Fancais d' Egypte (IFE) program and he thankful to Prof. Michel Etienne and Laure Vendier at the LCC for their support in the analysis.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

44_2017_1990_MOESM1_ESM.docx (14 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Department of Organometallic and Organometalloid ChemistryNational Research CentreCairoEgypt
  2. 2.Chemistry Department, Faculty of ScienceHelwan UniversityCairoEgypt
  3. 3.Labortoire de Chimie de Coordination du CNRS (LCC)Toulouse Cedex 4France
  4. 4.Botany and Microbiology Department, Faculty of Science (Boys)Al-Azhar UniversityCairoEgypt

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