Background: Schiff bases, which may be synthesised from
sulfonamide and aldehydes, have a broad range of biological effects in clinical
medicine, are also referred to as anticancer and antiviral medicines.
Sulfonamides and their derivatives are frequently reported for their
antibacterial, antiviral, antifungal, anticancer, and anti-inflammatory
properties.
Objective: The aim of the study was to synthesise new
derivatives of sulfonamide compounds containing azo and Schiff base fragments
and confirm the structures by 1H-NMR and FT-IR spectroscopy, as well as to
investigate the antibacterial activities against medically important Gram (+)
and Gram (-) bacterial strains.
Methods: Novel sulfonamide derivatives S1, S2, S3, A1, A2,
and A3 were synthesised and tested with Staphylococcus aureus and Pseudomonas
aeruginosa as well as against Candida albicans fungi. Studies on antimicrobial
agents were carried out using the agar diffusion method. Molecular docking was
used to study the theoretical binding of the compounds with some selected
proteins. Docking studies were carried out using the program MOE (2015.10).
Results: The results of antimicrobial evaluation revealed
that especially compounds of Schiff bases (S1, S2, and S3) exhibited good
activity against all microorganisms of bacteria and fungi as compared with A1,
A2, and A3. Against Candida albicans, it was found that compounds S1 and S3
gave the best activity, 21 and 20 mm, respectively. Antibacterial activity
showed that compound A2 gave the best activity (34 mm at 1000 µg/mL) against
Staphylococcus aureus. Other compounds S1, S2, S3, A1, and A3 gave very good
activities against the same bacteria, 29, 13, 29, 28, and 28 mm, respectively,
at the same concentration. Antibacterial activity against Pseudomonas
aeruginosa revealed that the compound S1 gave the best inhibition zone (25 mm)
at 1000 µg/mL, whereas compounds S2 and S3 showed good potent activity (15 and
20 mm, respectively). In Silico studies showed that free binding energy (S) of
the compounds against S. aureus using protein 1JIJ were -7.15 to -8.60 kcal/mol,
whereas free binding energy (S) using 5V5Z fungi protein gave the values -7.10
to -8.22 kcal/mol.
Conclusion: Schiff base derivatives exhibited superior
antimicrobial activity compared with azo derivatives. A clear correlation was
observed between the activity of the compounds and their molecular docking
through the high negative values of free binding energy. This investigation
revealed these compounds with binding energies that were on par with those of
typical medications. Additionally, these compounds were shown to be powerful
antibacterial agents bioactivity score and bioavailability radar analysis.
Author(s) Details
Munther Abduljaleel
Muhammad-Ali
Department of Ecology, College of Science, University of
Basrah, Basra, Iraq.
Ekhlas Qanber Jasim
Department of Pathology Analyses, College of Science, University of Basrah,
Basra, Iraq.
Abdullah H. Al-
Saadoon
Department of Pathology Analyses, College of Science, University of Basrah,
Basra, Iraq.
Please see the book here :- https://doi.org/10.9734/bpi/psnid/v9/6835
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