Abstract
New dipeptide–dihydroquinolinone derivatives were successfully synthesised by benzotriazole mediated nucleophilic acyl substitution reaction and their structures were elucidated by spectroscopic and analytic techniques. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. While all compounds showed moderate to good in vitro CA inhibitory properties against hCA IX and hCA XII with inhibition constants in the micromolar level (37.7–86.8 and 2.0–8.6 µM, respectively), they did not show inhibitory activity against hCA I and hCA II up to 100 µM concentration. The antioxidant capacity of the peptide–dihydroquinolinone conjugates was determined using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method. Most of the synthesised compounds showed low antioxidant activities compared to the control antioxidant compounds BHA and α-tocopherol.
Highlights
New dipeptide–dihydroquinolinone derivatives were successfully synthesised by benzotriazole mediated nucleophilic acyl substitution reaction and their structures were elucidated by spectroscopic and analytic techniques
The synthesis of the N-protected mono and dipeptide–dihydroquinolinone conjugates 1–6 is summarised in Scheme 1
Mono and dipeptide–dihydroquinolinone derivatives synthesised within the scope of this study were synthesised by benzotriazolemediated method with good yields
Summary
New dipeptide–dihydroquinolinone derivatives were successfully synthesised by benzotriazole mediated nucleophilic acyl substitution reaction and their structures were elucidated by spectroscopic and analytic techniques. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. While all compounds showed moderate to good in vitro CA inhibitory properties against hCA IX and hCA XII with inhibition constants in the micromolar level (37.7–86.8 and 2.0–8.6 mM, respectively), they did not show inhibitory activity against hCA I and hCA II up to 100 mM concentration. 2-Quinolinones derivatives constitute a privilege class of heterocyclic compounds for their wide range of important biological properties such as such as antibacterial, antimalarial, antitumor, carbonic anhydrase inhibitor, antioxidant, anti-tuberculosis, antiparasitic and anti-hepatit C and B viruses activity. Encouraged by the above literature information and our interest in the biological and chemical properties of such compounds, synthesis and carbonic anhydrase and antioxidant properties of mono and dipeptide containing dihydroquinolinone derivatives have been studied
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