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SYNTHESIS OF BIOLOGICALLY ACTIVE 6-(TOLYLHYDRAZINYLIDENE)PYRAZOLO[1,5-a]PYRIMIDINONES

Янина В. Бургарт, Наталья А. Елькина, Евгений В. Щегольков, Ольга П. Красных, Вера В. Маслова, Галина А. Триандафилова, Сергей Ю. Солодников, Галина Ф. Махаева, Ольга Г. Серебрякова, Елена В. Рудакова, Виктор И. Салоутин
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Abstract


New pyrazolo[1,5-a]pyrimidinones functionalized with the tolylhydrazone fragment were obtained as a result of cyclization of 3-oxo-
2-(tolylhydrazinylidene) esters with 3-aminopyrazoles. In this case, methyl- and trifluoromethyl-containing derivatives regioselectively
form pyrazolo[1,5-a]pyrimidin-7-ones, while cyclization of polyfluoroalkyl-substituted analogs can take place competitively with the formation of dihydropyrazolo[1,5-a]pyrimidin-5-ones, for which ring-chain isomerism is characteristic in solution. It was found that 6-(tolylhydrazinylidene)pyrazolo[1,5-a]pyrimidin-7-ones have a pronounced analgesic activity. The trifluoromethyl-containing analog
selectively inhibits carboxylesterase in micromolar concentration.

Authors: Olga P. Krasnykh, Vera V. Maslova, Galina A. Triandafilova, Sergey Yu. Solodnikov, Galina F. Makhaeva, Olga G. Serebryakova, Elena V. Rudakova, Victor I. Saloutin*


Keywords


pyrazolo[1,5-a]pyrimidinones; acute toxicity; analgesic activity; anticarboxylesterase activity; antiradical activity; ring-chain isomerism; regioisomers

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