Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds

Pintilie, Lucia; Tanase, Constantin; Maganu, Maria; Caproiu, Miron Teodor

Lucia Pintilie, Constantin Tanase, Maria Maganu, Miron Teodor Caproiu

Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds

Abstract:

Some 6,8-dichloro-quinolone compounds were designed and synthesized; by comparing with 6-fluoro-8-chloro-quinolone compounds, the influence of the nature of the halogen atom from six position of the quinolone ring on the molecular properties and on the antimicrobial activity was studied. The DFT/B3LYP/6-311G* level of basis set was used for the computation of molecular structure of optimized compounds. The calculations of characteristics and molecular properties were performed using Spartan’14 Software from Wavefunction, Inc. Irvine, CA. The HOMO-LUMO energies and orbitals, global reactivity descriptors, various thermodynamic parameters, and dipole moment (i) were calculated to determine the molecular properties of quinolone compounds. Molecular docking studies were realized to identify and visualize the most likely interaction ligand (quinolone/fluoroquinolone compounds) with the protein receptor. The score and hydrogen bonds formed with the amino acids from group interaction atoms are used to predict the binding modes, the binding affinities, and the orientation of the docked quinolone/fluoroquinolone derivatives in the active site of the protein receptor. The protein-ligand complex was realized based on the X-ray structure of Bacillus cereus (PDB ID: 1VEN) using CLC Drug Discovery Workbench 2.4 software. The quinolone compounds were characterized by physical-chemical methods (elemental analysis, IR spectral analysis, 1H-NMR, 13C-NMR spectra, UV-Vis, thin layer chromatography) and by antimicrobial activity against some Gram-positive and Gram-negative microorganisms: Staphylococcus aureus, Bacillus cereus, Bacillus subtilis, Micrococcus luteus, Escherichia coli and Pseudomonas aeruginosa.

Keywords:
quinolones; fluoroquinolones; molecular docking; antimicrobial activity

Issue: 2020, Volume 71, Issue 11

Pages: 10-21

Publication date: 2020/12/4

https://doi.org/10.37358/RC.20.11.8369

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
PINTILIE, L., TANASE, C., MAGANU, M., CAPROIU, M.T., Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds, Rev. Chim., 71(11), 2020, 10-21.

Vancouver
Pintilie L, Tanase C, Maganu M, Caproiu MT. Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds. Rev. Chim.[internet]. 2020 Nov;71(11):10-21. Available from: https://doi.org/10.37358/RC.20.11.8369

APA 6th edition
Pintilie, L., Tanase, C., Maganu, M. & Caproiu, M.T. (2020). Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds. Revista de Chimie, 71(11), 10-21. https://doi.org/10.37358/RC.20.11.8369

Harvard
Pintilie, L., Tanase, C., Maganu, M., Caproiu, M.T. (2020). 'Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds', Revista de Chimie, 71(11), pp. 10-21. https://doi.org/10.37358/RC.20.11.8369

IEEE
L. Pintilie, C. Tanase, M. Maganu, M.T. Caproiu, "Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds". Revista de Chimie, vol. 71, no. 11, pp. 10-21, 2020. [online]. https://doi.org/10.37358/RC.20.11.8369

Text
Lucia Pintilie, Constantin Tanase, Maria Maganu, Miron Teodor Caproiu,
Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds,
Revista de Chimie,
Volume 71, Issue 11,
2020,
Pages 10-21,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.11.8369.
(https://revistadechimie.ro/Articles.asp?ID=8369)
Keywords: quinolones; fluoroquinolones; molecular docking; antimicrobial activity

RIS
TY - JOUR
T1 - Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds
A1 - Pintilie, Lucia
A2 - Tanase, Constantin
A3 - Maganu, Maria
A4 - Caproiu, Miron Teodor
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 11
SP - 10
EP - 21
UR - https://doi.org/10.37358/RC.20.11.8369
KW - quinolones
KW - fluoroquinolones
KW - molecular docking; antimicrobial activity
ER -

BibTex
@article{RevCh2020P10,
author = {Pintilie Lucia and Tanase Constantin and Maganu Maria and Caproiu Miron Teodor},
title = {Design, Synthesis, Molecular Docking and Antibacterial Screening of some Quinolone Compounds},
journal = {Revista de Chimie},
volume = {71},
number = {11},
pages = {10-21},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.11.8369},
url = {https://revistadechimie.ro/Articles.asp?ID=8369}
}

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