Sinteza i fizičko-hemijska karakterizacija N-aromatičnih monosupstituisanih derivata karbohidrazona i tiokarbohidrazona

Abstract

U ovoj doktorskoj disertaciji je radi fizičko-hemijske karakterizacije i ispitivanja potencijalne biološke aktivnosti sintetisano 40 derivata mono(tio)karbohidrazona. Strukture dobijenih jedinjenja su potvrđene NMR i FT–IR spektroskopijom, elementalnom i rendgenskom strukturnom analizom. Uticaj rastvarača i prisutnog supstituenta na položaje apsorpcionih maksimuma ispitani su po principima LSER i LFER metoda. Teorijski proračuni za sintetisana jedinjenja izvedeni su primenom TD–DFT metode. Jonizacione konstante derivata mono(tio)karbohidrazona su određene potenciometrijskim titracijama. Antioksidativna aktivnost je određena primenom tri testa: DPPH, ABTS i FRAP testa. Antimikrobna aktivnost je ispitana mikrodilucionom metodom na dva soja bakterija: Staphylococcus aureus i Escherichia coli. Za jedinjenja koja su pokazali antimikrobnu aktivnost je ispitan procenat citotoksičnosti. Sveukupan zaključak o sličnosti i razlikama sintetisanih derivata izveden je na osnovu multivarijatnih metoda klaster analize i analize glavnih komponenti.

In this doctoral dissertation, 40 mono(thio)carbohydrazone derivatives were synthesized for the purpose of physico-chemical characterization and examination of potential biological activity. The structures of the obtained compounds were confirmed by NMR and FT –IR spectroscopy, elemental analysis and X-ray structural analysis. The influence of solvent and substituent present on the positions of absorption maxima was examined according to the principles of LSER and LFER methods. Theoretical calculations for the synthesized compounds were performed by the TD–DFT method. The acid constants of mono(thio)carbohydrazone derivatives were determined by potentiometric titrations. Antioxidant activity was determined using three tests: DPPH, ABTS and FRAP test. Antimicrobial activity was examined by microdilution method on two strains of bacteria: Staphylococcus aureus and Escherichia coli. The percentage of cytotoxicity was examined for compounds that showed antimicrobial activity. Overall conclusion about the similarities and differences of the synthesized derivatives was studied by multivariate methods of cluster analysis and analysis of principal components.