Synthesis, X-ray structural determination and biological evaluation of novel ferrocene grafted spiroquinoxalinopyrrolidine

Synthesis of a hybrid heterocycle comprising ferrocene, spiropyrrolidine and quinoxaline structural moieties have been achieved in good yield via ionic liquid expedited multicomponent 1,3-dipolar cycloaddition reaction. Structural properties of the synthesized compound were exploited using single crystal X- ray crystallographic studies. Hirshfeld analysis revealed the importance of H center dot center dot center dot H (59.6%), C-H center dot center dot center dot pi (22.4%) and N center dot center dot center dot H (3.5%) contacts within the molecular packing. The Fe-C interactions around ferrocenyl moiety were investigated using Natural Bond Orbital (NBO) and Atoms In Molecules (AIM) calculations. A predominant covalent character of interactions between Fe-C were been accessed from AIM calculation. A weaker extend of pi-back donation appeared in cyclopentadienyl moiety carrying the substituent instead of unsubstituted one. Further, the in vitro antimicrobial potential of the synthesized compound against five food borne bacterial pathogens reveals its significant activity against E. coli and S. enterica with MIC values 6.00 mu g/mL and 8.00 mu g/mL, respectively. The antioxidant activity of compound 5 was found to be 84.37 +/- 0.55 at 250 mu g/mL concentration with an IC50 value = 33.80 mu g/mL. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

A hybrid heterocycle comprising ferrocene, spiropyrrolidine, and quinoxaline structural moieties was synthesized in good yield via ionic liquid expedited multicomponent 1,3-dipolar cycloaddition reaction. Structural properties were studied using single crystal X-ray crystallographic studies, while Fe-C interactions and antimicrobial potential were investigated through NBO and AIM calculations. The compound showed significant antimicrobial activity against E. coli and S. enterica, as well as antioxidant activity with an IC50 value of 33.80 μg/mL.