Синтез, протибактеріальна та протигрибкова дія нових 4-амінозаміщених піразоло[1,5-а]піразинів

• Дата: 2018
• Автори: Hrynyshyn, Ye. V., Musiichuk, H. R., Tsyzoryk, N. M., Grozav, A. M., Yakovychuk, N. D., Bol’but, A. V., Vovk, M. V.
• Формат: Стаття
• Мова: Ukrainian
• Опубліковано: National University of Pharmacy 2018
• Теми: electrophilic substrates; amination; 4-aminopirazolo[1; 5-a]pyrazines; antibacterial and antifungal activity; UDC 547.77 547.866 615.31; электрофильные субстраты; аминирование; 4-аминопиразоло[1; 5-a]пиразины; противобактериальная и противогрибковая активность; УДК 547.77 547.866 615.31; електрофільні субстрати; амінування; 4-амінопіразоло[1; 5-a]піразини; протибактеріальна та протигрибкова активність
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.18.944
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

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).