Cинтез та гіпоглікемічна активність похідних 4-піразоліден-3-карбонових кислот, екзофункціоналізованих гідразиніліден-1,3-тіазолідиновим фрагментом

• Datum: 2015
• Hauptverfasser: Bratenko, M. K., Barus, M. M., Denysenko, O. M., Rodik, R. V., Vovk, M. V., Yarosh, O. K.
• Format: Artikel
• Sprache: Ukrainian
• Veröffentlicht: National University of Pharmacy 2015
• Schlagworte: 4-формілпіразол-3-карбонові кислоти; тіосемікарбазони; діетилацетилендикарбоксилат; 1; 3-тіазолідин-4-они; циклоконденсація; гіпоглікемічна активність; УДК 547.771 547.789 615.012.1; 547.79
• Online Zugang: https://ophcj.nuph.edu.ua/article/view/ophcj.15.837
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

It has been shown that 4- formylpyrazole-3-carboxylic acids and their ethyl esters interact selectively with thiosemicarbazide and its N4-aryl-derivatives in boiling acetic acid with formation of the corresponding 4-pyrazolylthiosemicarbazones with the yields of 76-91%. It has been found that heating of 4-pyrazolylthiosemicarbazones with diethyl acetylenedicarboxylate in boiling ethanol for 3 hours leads to formation of 1,3-thiazolidine-containing polyfunctional pyrazole derivatives with yields of 73-95%. Formation of compounds of this type indicates that the process occurs according to the scheme of the primary attack of a highly electrophilic triple bond of acetylenedicarboxylate by the nucleophilic atom of sulfur of the thiosemicarbazone fragment with subsequent intramolecular condensation, which leads to formation of the 4-oxo-1,3-thiazolidine-5-ilidene cycle. The structure of the 1,3-thiazolidinilidenehydrazonepyrazoles synthesized has been proven by a complex of spectral methods; the most informative of them are 13C NMR spectra with signals of carbon atoms of the thiazolidine cycle: C4 (159-161 ppm), C2 (162-165 ppm), C5 (163-165 ppm), as well as of the exo-cyclic ethoxycarbonylethylidene fragment: HC= (114-118 ppm); and of C(O) O (165 ppm). It has been determined that the compounds synthesized cause the hypoglycemic dose-dependent effect in mice, which is much more potent than the same effect of the reference medicine – pioglitazone.