A new class of β-aryloxyquinoline based diversely fluorine substituted N-aryl quinolone derivatives 8a-x have been synthesized via a one-pot multicomponent reaction. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 8g, 8h, 8m, 8q and 8v exhibited excellent antimicrobial activity compared with first line drugs. In vitro antituberculosis activity was evaluated against Mycobacterium tuberculosis H37Rv and compounds 8h and 8q emerged as the promising antimicrobial member with better antituberculosis activity. The brine shrimp bioassay was carried out to study the in vitro cytotoxic properties of the synthesized compounds. In vitro antioxidant activity was evaluated by ferric-reducing antioxidant power method. Compounds 8e, 8k, 8l, 8s, 8u and 8w showed highest antioxidant potency.