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

Younes Lakhrissi; Mohamed Rbaa; Burak Tuzun; Abdelhadi Hichar; El Hassane Anouar; Khadija Ounine; Faisal Almalki; Taibi Ben Hadda; Abdelkader Zarrouk; Brahim Lakhrissi

doi:10.1016/j.molstruc.2022.132683

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

Younes Lakhrissi, Mohamed Rbaa, Burak Tuzun, Abdelhadi Hichar, El Hassane Anouar, Khadija Ounine, Faisal Almalki, Taibi Ben Hadda, Abdelkader Zarrouk, Brahim Lakhrissi

Chemistry

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48 Scopus citations

Abstract

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.

Original language	English
Article number	132683
Journal	Journal of Molecular Structure
Volume	1259
DOIs	https://doi.org/10.1016/j.molstruc.2022.132683
State	Published - 5 Jul 2022

Keywords

8-Hydroxyquinoline
Antibacterial activity
Docking
POM (Petra/Osiris/Molinspiration) analyses
Synthesis

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10.1016/j.molstruc.2022.132683

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Lakhrissi, Y., Rbaa, M., Tuzun, B., Hichar, A., Anouar, E. H., Ounine, K., Almalki, F., Hadda, T. B., Zarrouk, A., & Lakhrissi, B. (2022). Synthesis, structural confirmation, antibacterial properties and bio-informatics computational analyses of new pyrrole based on 8-hydroxyquinoline. Journal of Molecular Structure, 1259, Article 132683. https://doi.org/10.1016/j.molstruc.2022.132683

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abstract = "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.",

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doi = "10.1016/j.molstruc.2022.132683",

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T1 - Synthesis, structural confirmation, antibacterial properties and bio-informatics computational analyses of new pyrrole based on 8-hydroxyquinoline

AU - Lakhrissi, Younes

AU - Rbaa, Mohamed

AU - Tuzun, Burak

AU - Hichar, Abdelhadi

AU - Anouar, El Hassane

AU - Ounine, Khadija

AU - Almalki, Faisal

AU - Hadda, Taibi Ben

AU - Zarrouk, Abdelkader

AU - Lakhrissi, Brahim

PY - 2022/7/5

Y1 - 2022/7/5

N2 - 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.

AB - 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.

KW - 8-Hydroxyquinoline

KW - Antibacterial activity

KW - Docking

KW - POM (Petra/Osiris/Molinspiration) analyses

KW - Synthesis

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U2 - 10.1016/j.molstruc.2022.132683

DO - 10.1016/j.molstruc.2022.132683

M3 - Article

AN - SCOPUS:85126272117

SN - 0022-2860

VL - 1259

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

M1 - 132683

ER -

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

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Keywords

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