Stereoselective synthesis, structural determination, computational studies and antimicrobial activity of novel class of spiropyrroloquinoxaline engrafted ferrocenoindole hybrid heterocycle
Journal of Molecular Structure, vol.1252, 2022 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 1252
- Publication Date: 2022
- Doi Number: 10.1016/j.molstruc.2021.132131
- Journal Name: Journal of Molecular Structure
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
- Keywords: Antimicrobial inhibition, Computational study, Ferrocene, Spiropyrrolidine, Structural determination
- Ondokuz Mayıs University Affiliated: Yes
Abstract
Our synthetic approach for the assembly of highly diversified spiropyrrolidine grafted ferrocene was based on a one-pot four component cascade reaction protocol involving 1,3-dipolar cycloaddition reaction of (E)-3-ferrocene-1-(4-bromophenyl)prop‑2-en-1-one and azomethine ylide generated in situ from quinoxalinone and L-tryptophan. The structure of the compound was assigned by one- and two-dimensional NMR spectroscopic studies. The regio- and stereochemistry of the spirocompound was confirmed by single crystal X-ray diffraction analysis. The nature of three-dimensional orientation of the synthesized compound has been investigated through single crystal X-ray diffraction study. Crystal structure of the synthesized compound was analyzed using Hirshfeld calculations. In spirocompound, the packing of molecules is controlled by significant O…H (3.3%), N…H (4.1%) and C[sbnd]H…π (24.8%) interactions. The different π-donation and π-back donation interactions was analysed using NBO calculations. The compound 6 exhibited potent inhibitory activity against tested MDR S. aureus strains ranging from 8.00 to 256.00 µg/mL with respect to MIC and MBC determination.