Synthesis, structural confirmation, antibacterial properties and bio-informatics computational analyses of new pyrrole based on 8-hydroxyquinoline

•Synthesis of new heterocyclic compound based on 8-hydroxyquinoline with different advantages.•Theoretical optimization by DFT (Density Functional Theory) level of theory and Mechanistic study by molecular docking .•Screening “in vitro” against E. coli, S. aureus and P. aeruginosa by means the disk...

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Published in:Journal of molecular structure 2022-07, Vol.1259, p.132683, Article 132683
Main Authors: Lakhrissi, Younes, Rbaa, Mohamed, Tuzun, Burak, Hichar, Abdelhadi, Anouar, El Hassane, Ounine, Khadija, Almalki, Faisal, Hadda, Taibi Ben, Zarrouk, Abdelkader, Lakhrissi, Brahim
Format: Article
Language:English
Subjects:
8-Hydroxyquinoline
Antibacterial activity
Docking
POM (Petra/Osiris/Molinspiration) analyses
Synthesis
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Summary:•Synthesis of new heterocyclic compound based on 8-hydroxyquinoline with different advantages.•Theoretical optimization by DFT (Density Functional Theory) level of theory and Mechanistic study by molecular docking .•Screening “in vitro” against E. coli, S. aureus and P. aeruginosa by means the disk method.•Discovered the ideal structural topology to inhibit Gram (+) and Gram (-) bacteria.•Identification of pharmacophore sites and toxicity risks by the use of Petra/Osiris/Molinspiration (POM). This study aims to synthesize new pyrrolic compounds derivatives of 8-hydroxyquinoline, explore the structure-activity relationship and the effect of the substituents carried by the pyrrole ring on their antibacterial properties. These compounds were characterized by IR, 1H, 13C NMR and elemental analysis. The NMR predicted chemical shifts were determined by the GIAO approach and the solvent effect was taken into account using the polarizable continuum model (PCM). The evaluation of the antibacterial activity was carried out "in vitro" against three bacterial strains namely; E. coli (ATCC35218), S. aureus (ATCC29213) and P. aeruginosa (ATCC27853) using the disk method. The results of antibacterial activity were compared with those of a standard antibiotic (Norfloxacin). The Minimum Inhibitory Concentrations (MICs) were calculated and discussed. The results of the experimental tests were supported by bioinformatics Docking, DFT and POM studies.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2022.132683