Quinoline based furanones and their nitrogen analogues: Docking, synthesis and biological evaluation.

A small library of twenty-four quinoline based butenolides also known as furanones and their nitrogen analogues was prepared by using two different aroylpropionic acids, viz. 3-(2-naphthoyl)propionic acid () and 3-(biphenyl-4-yl)propionic acid (), as starting materials. The 3-aroylpropionic acids were reacted with different 6-substituted-2-chloroquinolin-3-carbaldehydes () to obtain the corresponding furan-2(3)-ones (). The purified and characterized furanones were then converted into their corresponding 2(3)-pyrrolones () and -benzyl-pyrrol-2(3)-ones (). The antimicrobial activities of the title compounds were evaluated against two strains of each Gram +ve ( and ), Gram -ve bacteria ( and ) and against fungal strains of and . anti-inflammatory potential of the title compounds was investigated by standard method. Majority of the compounds showed significant antibacterial activity against both the Gram +ve strains. Eight most potent anti-inflammatory compounds ( which exhibited >53% inhibition in edema, were also screened for their analgesic activity. All the tested compounds were found to have significant reduction in ulcerogenic action but only three compounds ( and ) showed comparable analgesic activity to standard drug, diclofenac. The results were also validated using approach and maximum mol doc score was obtained for compounds . On comparing the and results of synthesized compounds, -benzyl pyrrolones () emerged as the potent anti-inflammatory agents. It was also observed that compounds that possess electron withdrawing group such as -Cl or NO are more biologically active.