Potent biological investigation into a new class of sulfone derivatives endowed with quinolinyl–cyclopropane analogue

Abstract

Novel series of quinoline derivatives incorporating cyclopropyl ring and sulfone linkage as substituents were synthesized, Oxidation of ethyl-2-cyclopropyl-4-(substituted phenylthio) quinoline-3-carboxylate 10a-n was carried out to set ethyl-2-cyclopropyl-4(substituted phenyl sulfonyl) quinoline-3-carboxylate 11a-n. Sulfone derivatives were afforded by reaction of glacial acetic acid and 30% hydrogen peroxide at room temperature. An eco-friendly synthesis of sulfone derivatives were afforded by using weak acid at room temperature. The synthesized quinoline incorporating sulfone linkage derivatives were evaluated for their expected antimicrobial activity; where the majority of these compounds showed potent antibacterial and antifungal activities against the tested strains of bacteria and fungi. All the final synthesized derivatives were characterized by their melting point, mass spectra, IR, 1 H NMR and 13 C NMR spectras. SAR and HOMO-LUMO studies were also carried out for proving the structural biological activity. Among them compounds 11a, 11b, 11h, 11k and 11m gave best results as their energy gap is very low which makes their activity higher.