Синтез і біологічна дія тіосемікарбазонів та (1,3-тіазол-2-іл)-гідразонів [(1-арил- 5-формілімідазол-4-іл)тіо]оцтових кислот

V. O. Chornous; A. O. Palamar; A. M. Grozav; I. M. Yaremiy; M. V. Vovk

doi:10.24959/ophcj.13.774

Authors

V. O. Chornous Bukovinian State Medical University, Ukraine
A. O. Palamar Bukovinian State Medical University, Ukraine
A. M. Grozav Bukovinian State Medical University, Ukraine
I. M. Yaremiy Bukovinian State Medical University, Ukraine
M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.13.774

Keywords:

[(1-aryl-5-formylimidazol-4-yl)thio]acetic acids, thiosemicarbazones, (1, 3-thiazol-2-yl)hydrazones, monochloroacetic acid, maleic anhydride, thiotriazoline, antioxidant and antimicrobial action

Abstract

This research focuses on the synthesis of thiosemicarbazones [(1-aryl-5-formylimidazol-4-yl)thio]acetic acids and the study of some of their chemical transformations and biological activity. By condensation of [(1-aryl-5-formylimidazol-4-il)thio]acetic acids with thiosemicarbazide in boiling acetic acid the corresponding thiosemicarbazones have been obtained with high yields. They were used as effective N,S-binucleophiles in reactions of cyclocondensation with electrophilic reagents. In particular, heating of these thiosemicarbazones with monochloroacetic acid in the acetic acid medium results in formation of (1,3-thiazol-2-il)hydrazones [(1-aryl-5-formylimidazol-4-yl)thio]acetic acids. By the reaction of maleic anhydride with thiosemicarbazones of [(1-aryl-5-formylimidazol-4-il)thio]acetic acids in boiling dioxane 2-[(1H-imidazol-5-yl)methylenehydrazino)-4-oxo-1,3-thiazole-5-il]acetic acids have been synthesized. The compounds obtained show a moderate antioxidant effect. The maximum level of inhibition of free radical lipids oxidation in vitro is observed in final concentrations of 10-1M and is 31.94% compared to the control. The results of the bactericidal and fungicidal activity obtained show that the compounds studied are characterized by the moderate antimicrobial action: the minimal bacteriostatic and fungistatic concentrations are in the range of 62.5-2000 mcg/ml.

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