Synthesis, the antibacterial and antifungal action of 4-aminopyrazolo[1,5-a]pyrazines

Authors

  • Ye. V. Hrynyshyn National University of Kyiv-Mohyla Academy, Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • H. R. Musiichuk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • N. M. Tsyzoryk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • A. M. Grozav Bukovinian State Medical University, Ukraine
  • N. D. Yakovychuk Bukovinian State Medical University, Ukraine
  • A. V. Bol’but Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.18.944

Keywords:

electrophilic substrates, amination, 4-aminopirazolo[1, 5-a]pyrazines, antibacterial and antifungal activity

Abstract

Aim. To create a convenient preparative method for the synthesis of new 4-aminopirazolo[1,5-a] pyrazines derivatives and perform the screening of their antibacterial and antifungal properties.
Results and discussion. It was determined that 4-chloropyrazolo[1,5-a]pyrazines selectively reacted with various alkylamines producing the corresponding 4-aminopyrazolo[1,5-a]pyrazines with high yields. The biological screening of the derivatives synthesized allowed us to identify compounds with the antibacterial and antifungal activity in the concentrations of 31.25-250 μg/ml.
Experimental part. The new 4-aminopyrazolo[1,5-a]pyrazines derivatives were produced by the reaction of 4-chloropyrazolo[1,5-a]pyrazines with the primary and secondary alkylamines at room temperature or by refluxing in ethanol. The structures of the compounds synthesized were confirmed with 1H, 13C NMR-spectra and mass spectra. The results of the microbiological screening using a micromethod of double serial dilutions in a liquid nutrient medium showed that the compounds synthesized exhibited a moderate bactericidal activity.
Conclusions. It has been found that the reaction of 4-chloropyrazolo[1,5-a]pyrazines with the primary and secondary alkylamines is a convenient method for the synthesis of aminopirazolo[1,5-a]pyrazines that exhibit a moderate antimicrobial activity against S. aureus 209, B. subtilis ATCC 6633, M. luteus ATCC 4698 (bacteria) and the antifungal activity against C. ablicans 669/1080 and C. krusei ATCC 6258 (fungi).

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Published

2018-09-19

How to Cite

(1)
Hrynyshyn, Y. V.; Musiichuk, H. R.; Tsyzoryk, N. M.; Grozav, A. M.; Yakovychuk, N. D.; Bol’but, A. V.; Vovk, M. V. Synthesis, the Antibacterial and Antifungal Action of 4-aminopyrazolo[1,5-a]pyrazines. J. Org. Pharm. Chem. 2018, 16, 45-49.

Issue

Section

Original Researches