Synthesis, characterization, biological evaluation and docking studies of 2′-[(2″,4″-difluorobiphenyl-4-yl)carbonyl]-1′-aryl-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-ones

•A series of novel spiropyrrolizidines were regioselectively synthesized.•Sensing ability to different metal ions and solvatochromic study on 5a were performed.•In vitro antimicrobial activity and cytotoxic studies were carried out.•Theoretical calculations under DFT were performed for 5a-h.

A series of novel 2′-[(2″,4″-difluorobiphenyl-4-yl)carbonyl]-1′-aryl-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-ones were regioselectively synthesized by multicomponent reaction with excellent yield. They were characterized by elemental analysis and various spectral techniques. Sensing ability of the compound to different metal ions was investigated. To ascertain the inhibitory activity of the compounds they were subjected to in vitro antimicrobial studies against various microbes and cytotoxic studies against Hep-2 cell line. The ligand-receptor interaction of the compounds was explored by molecular docking and the human folate receptor (4LRH) was identified as the potential target protein. DFT calculations were incorporated in the study to compare the molecular structure and geometrical parameters of 2′-[(2″,4″-difluorobiphenyl-4-yl)carbonyl]-1′-phenyl-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-one with experimental data.

Graphical abstractHighly efficient 2′-[(2″,4″-difluorobiphenyl-4-yl)carbonyl]-1′-aryl-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indole-3,3′-pyrrolizin]-2(1H)-ones with better inhibitory activity against various microbes were synthesized.Figure optionsDownload full-size imageDownload as PowerPoint slide