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Rezime: U ovoj disertaciji sintetisana je serija acilpiruvata u visokim prinosima reakcijom Klajzenove kondenzacije. Acilpiruvati su zatim korišćeni kao prekursori za sintezu tri nove klase jedinjenja pod pretpostavkom da će pokazati bolja biološka svojstva od samih acilpiruvata. Sintetisana je serija od dvadeset i pet novih 1,5- diaril-4-(2-tienilkarbonil)-3-hidroksi-3-pirolin-2-oni. Pored toga, bilo je veoma interesantno ispitati kako koordinacija za neke jone prelaznih metala utiče na aktivnost organskih molekula kao što su acilpiruvati. Zbog toga je sintetisano jedanaest novih metalo-organskih kompleksa sa acilpiruvatima kao ligandima koji sadrže Cu2+ ili Pd2+ kao centralni jon metala. Sva novo-sintetisana jedinjenja su okarakterisana spektroskopskom analizom (UV-Vis, IR, 1H i 13C NMR), masenom spektrometrijom i elementalnom analizom. Rendgenska strukturna analiza je takođe urađena gde je to bilo moguće. Novosintetizovani molekuli testirani su na antioksidativni, antimikrobni i antitumorski potencijal. DPPH test pirolidinona je pokazao da ova jedinjenja poseduju dobru antioksidativnu aktivnost (najniža IC50 vrednost iznosi 166,75 µg/ml). Ovaj test je takođe pokazao da većina acilpiruvata poseduje bolju antioksidativnu aktivnost od odgovarajućih metalo-organskih jedinjenja bakra(II). Ispitivanja antimikrobne aktivnosti su otkrila da pirolidinoni pokazuju značajnu inhibitorsku aktivnost na soju bakterija Staphylococcus aureus u prilično niskim koncentracijama (najniža izmerena MIC vrednost iznosi 0,312 mg/ml), dok je najosetljiviji soj gljivica bio Trichophyton mentagrophytes sa najnižom MIC od 0,625 mg/ml. MIC vrednosti za metalo-organska jedinjenje bakra(II) na testiranim mikroorganizmima bile su u rasponu od 0,048 do 3,125 mg/ml. Najosetljiviji soj bakterija bio je Proteus mirabilis, dok je među gljivicama najosetljiviji soj bio Candida albicans. SUMMARY: In this dissertation a series of acylpyruvates in high yields has been synthesized using the Claisen condensation reaction, which were then used as precursors for the synthesis of three new classes of compounds. Three new classes of compounds were synthesized under the assumption that they would show better biological properties than the acylpyruvates themselves. A series of twenty-five novel and one previously published 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3- pyrrolin-2-ones were synthesized. In addition, it was very interesting to examine how coordination for some metal ion affects the activity of organic molecules such as acylpyruvates, and therefore eleven new metal-organic complexes were synthesized with acylpyruvates as ligands containing Cu2+ or Pd2+ as the central metal ion. All newly synthesized compounds were characterized by spectroscopic analysis (UV-Vis, IR, 1H and 13C NMR), mass spectrometry and elemental analysis. X-ray structural analysis was also performed where possible. The newly synthesized molecules were tested for antioxidant, antimicrobial and antitumor potential. The DPPH test showed that most acylpyruvates showed better antioxidant activity than the corresponding metal-organic copper(II) compounds. MIC values for the metalorganic copper(II) compounds on the tested microorganisms were in range from 0.048 to 3.125 mg/ml. The most sensitive bacteria strain was Proteus mirabilis, while among the fungi the most sensitive strain was Candida albicans. The results of the antitumor activity showed that these compounds showed good cytotoxic activity. All metal-organic copper(II) compounds showed lower IC50 values on the LS174 and A549 cell lines compared to cisplatin. The results of the antitumor potential for palladium(II) metal-organic complexes showed that the three compounds had very good cytotoxic activity on HeLa cells and significant activity on MDA-MB 231 cells. The results obtained by examining the interations between the palladium compound and cisplatin indicate that these compounds may be useful as adjuvants in therapy for the treatment of tumors, reducing the doses of cisplatin and thus the side effects of this drug.