Synthesis, characterization and investigation of bioactive properties of thiophene based imine and phosphoazometine compound

In recent years, the loss of effectiveness of existing marketed drugs with the development of drug resistance has created a new focus in drug discovery and development studies. In this context, synthesis and characterization of new compounds gain more importance. In this study, thiophene-based imine ((E)-N,N-dimethyl-4-((thiophen-2-yl-methylene)amino)aniline) (Y6), amine (N1,N1-dimethyl-N4-(thiophene-2) -ylmethyl)benzene-1,4-diamine) (Y6a) and phosphoasomethine (Diphenyl (((4-(dimethylamino)phenyl) amino)(thiophen-2-yl)methyl)phosphate) (Y6b) compounds, was synthesized, and the structure were analyzed using FT-IR, 1H-NMR, and 13C-NMR techniques. Then, the bioactive properties of the synthesized compounds were investigated. All compounds were found to have significant antioxidant properties. It was observed that compound Y6a (IC50: 5,13 µM) had significantly higher radical scavenging activity than ascorbic acid (IC50: 17.55 µM). All compounds showed strong inhibitory effects against hCA I and II isoforms. The IC50 values of Y6, Y6a and Y6b compounds were found to be 1,96, 8,25 and 0,459 µM for hCA I and 1,89, 0,56 and 1,02 µM for hCA II isoenzyme, respectively. The antimicrobial test results showed that the compounds did not have antifungal activity against C. albicans and C. tropicalis strains, but had antibacterial activities against all bacterial strains used. In addition, it was observed that all three compounds exhibited good antiproliferative activity in the MCF-7 cell line, causing a decrease in the growth curve velocity on the basis of cell index with the increase in concentration compared to control cells. The IC50 values of Y6, Y6a and Y6b compounds were determined as 56,58, 51,30 and 40,01 µM, respectively. Compound Y6b showed an effect with cisplatin, one of the effective chemotherapeutic drugs, at a close IC50 value (40.01 µM). The results obtained show that these compounds both have an inhibitory effect on hCA I and hCA II enzymes and have antibacterial, anticancer and antioxidant activity. It is thought that these results will provide an important resource for new drug designs and pharmacological applications. Keywords: Imine, Phosphoasomethine, Cytotoxic activity, Antimicrobial activity, Antioxidant activity, Carbonic anhydrase inhibition