Synthesis of bis-sulfide, bis-sulfone and β-amino carbonylcompounds containing cyclhekzanone structure andenzyme inhibition (hCA I,hCA II, AChE ve BChE) studies

In the thesis, bis-chalcone compounds (1a-j) were synthesized by the Claisen- Schmidt condensation reaction of the cyclohexanone compound with various aromatic aldehyde derivatives. The bis-sulfide derivatives (2a-j) were synthesized by adding 1,4- Michael type of thiophenol compound to bis-chalcone derivatives. Bis-sulfone derivatives (3a-j) were synthesized by oxidizing bis-sulfide compounds with metachloroperbenzoic acid (m-CPBA). For the synthesis of β-amino carbonyl compounds, 1,4-Michael type addition reactions were tried. Since the product was not obtained in 1,4- Michael addition trials, bis-β-amino carbonyl compounds (4a-e) and mono-β-amino carbonyl compounds (5a-e) were synthesized by multicomponent Mannich-type reaction as an alternative. The structure of all the intermediate and final products synthesized in the scope of the thesis was characterized by spectroscopic methods (1H-NMR, 13C-NMR, FT-IR) and elemental analysis technique. Some of the synthesized bis-sulfite (2h, 2i and 2j) and mono-β-amino carbonyl compounds (5a, 5d and 5e) were obtained from single crystals and their structures was determined by X-ray crystallography. Inhibition studies of bissulfide (2a-j), bis-sulfone (3a-j) and β-amino carbonyl compounds (4a-e and 5a-e) against human carbonichydrase enzymes (hCA I, hCA II), acetylcholinesterase enzyme (AChE) and butyrylcholinesterase enzyme (BChE) were performed.