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


TOSUN G., Arslan T., ISKEFIYELI Z., KÜÇÜK M. , KARAOGLU S. A. , YAYLI N.

TURKISH JOURNAL OF CHEMISTRY, vol.39, no.4, pp.850-866, 2015 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 39 Issue: 4
  • Publication Date: 2015
  • Doi Number: 10.3906/kim-1501-112
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.850-866
  • Keywords: Quinoline derivatives, flavonones, air oxidation, antimicrobial activity, antituberculosis activity, antioxidant activity, SOLVENT-FREE CONDITIONS, RUTA-GRAVEOLENS L., QUINOLINE DERIVATIVES, CORRESPONDING 2-ARYL-2,3-DIHYDROQUINOLIN-4(1H)-ONES, ANTIOXIDANT ACTIVITIES, FACILE SYNTHESIS, EFFICIENT, CATALYST, CYCLIZATION, 2'-AMINOCHALCONES

Abstract

Three new series of 33 quinolone compounds, 2-(2-, 3-, and 4-fluoropheny1)-4-0-alkyl(C5-15) quinolines (7a-k, 8a-k, and 9a-k), were synthesized from 2-(2-, 3-, and 4-fluoropheny1)-2,3-dihydroquinolin-4(1H)-one (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 (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 (MIC) of 62.5-500 mu g/mL, indicating their potential uses as antituberculosis agents. Among them 8a-k (m-fluoride) were the most active compounds against M. smegmatis (MIC, 62.5-125 mu g/mL). The newly synthesized title compounds were also evaluated for their in vitro antioxidant activities using DPPH center dot radical scavenging and FRAP tests. They showed at a low concentration (mg/mL) a range of SC50 values of 0.03-12.48 mg/mL (DPPII center dot.) and 0-722 mu M (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.