Synthesis, characterization and determination of enzyme activities of new tetralone-based 3-cyano quinoline derivatives

Quinoline and cyanopyridine derivatives have an important place in organic and medicinal chemistry due to their biological activities. In this study, the synthesis of new hybrid molecules containing two units in the same structure and the investigation of their inhibitory effects against CA enzymes were aimed. For this purpose, firstly, tetralone based chalcone analogs were synthesized by reacting 1-tetralone with the related benzaldehyde derivatives in basic medium. The synthesized chalcone analogs were reacted with malonitrile in methanol and in the presence of K2CO3 to synthesize the target compounds 4-(aryl)-2-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile deriva-tives. After the structures of the obtained compounds were elucidated by spectroscopic methods (IR, 1H-NMR, 13C-NMR), their enzyme inhibitory effects against hCA I and hCA II isoenzymes were investigated. It was observed that 4-(3-chlorophenyl)-2-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (5f) had the highest inhibition against hCA I enzyme, while 2-methoxy-4-(4-methoxyphenyl)-5,6-dihydrobenzo [h]quinoline-3-carbonitrile (5c) had the highest inhibition against hCA II enzyme.