Synthesis and biological evaluation of a new series of 4-alkoxy-2-arylquinoline derivatives as potential antituberculosis agents

Authors : Gonca TOSUN, Tayfun ARSLAN, Zeynep İSKEFİYELİ, Murat KÜÇÜK, Şengül Alpay KARAOĞLU, Nurettin YAYLI

Pages : 850-866

Doi:10.3906/kim-1501-112

View : 30 | Download : 13

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Three new series of 33 quinolone compounds, 2-insert ignore into journalissuearticles values(2-, 3-, and 4-fluorophenyl);-4-O-alkylinsert ignore into journalissuearticles values(C$_{5-15});$quinolines insert ignore into journalissuearticles values(7a-k, 8a-k, and 9a-k);, were synthesized from 2-insert ignore into journalissuearticles values(2-, 3-, and 4-fluorophenyl);-2,3-dihydroquinolin-4insert ignore into journalissuearticles values(1H);-one insert ignore into journalissuearticles values(4, 5, and 6); by the reaction of alkyl halides under basic conditions in DMF. The new compounds 7a-k, 8a-k, and 9a-k were synthesized from flavonones 4-6, which can be considered new precursors for quinoline synthesis through a one-step reaction. All the target compounds insert ignore into journalissuearticles values(7a-k, 8a-k, and 9a-k); were evaluated for their in vitro antimicrobial activity against nine test microorganisms. They showed the most activity against Mycobacterium smegmatis with minimum inhibitory concentrations insert ignore into journalissuearticles values(MIC); of 62.5-500 $\mu $g/mL, indicating their potential uses as antituberculosis agents. Among them 8a-k insert ignore into journalissuearticles values(m-fluoride); were the most active compounds against M. smegmatis insert ignore into journalissuearticles values(MIC, 62.5-125 $\mu $g/mL);. The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH• radical scavenging and FRAP tests. They showed at a low concentration insert ignore into journalissuearticles values(mg/mL); a range of SC$_{50}$ values of 0.03-12.48 mg/mL insert ignore into journalissuearticles values(DPPH•); and 0-722 $\mu $M insert ignore into journalissuearticles values(FRAP);, respectively. The antioxidant results of compounds 7a-k, 8a-k, and 9a-k revealed that the length of the alkyl chain was negatively correlated with antioxidant capacity.
Keywords : Quinoline derivatives, flavonones, air oxidation, antimicrobial activity, antituberculosis activity, antioxidant activity