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| Home > Publications database > Schiff Base Derivatives of Benzothiazole and Benzamide as Promising Antimicrobial Agents: Integrated In Silico and In Vitro Evaluation. |
| Home > Publications database > Schiff Base Derivatives of Benzothiazole and Benzamide as Promising Antimicrobial Agents: Integrated In Silico and In Vitro Evaluation. |
| Journal Article | DKFZ-2026-02267 |
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2026
Wiley-VCH
Weinheim
Abstract: Antimicrobial resistance (AMR) remains a critical global health challenge, demanding new scaffolds with potent and broad-spectrum activity. In this work, a library of Schiff-base derivatives of benzothiazoles (2a-2f) and benzamides (5a-5i) was designed, synthesised via a microwave-assisted approach, and comprehensively characterised by 1H-/13C-NMR, FT-IR, and UV-Vis spectroscopy. In silico ADMET profiling predicted favourable pharmacokinetics and low toxicity. Molecular docking of the compounds against E. coli glucosamine-6-phosphate synthase (2VF5) and C. albicans lanosterol 14α-demethylase (5V5Z) revealed strong binding affinities, surpassing ciprofloxacin and fluconazole. Compounds 5f and 2f (-8.1 and -8.0 kcal/mol) for 2VF5, while 2a and 5h had good binding affinity (-9.7 and -9.6 kcal/mol) for 5V5Z, showing optimal interactions with key catalytic residues, maintaining structural stability in molecular dynamics simulations. Consistent with these predictions, compounds 5h, 5f, and 2a exhibited potent antibacterial activity (MIC: 3.13-12.5 µg/mL) against both Gram-positive and Gram-negative strains, and antifungal activity (MIC: 6.25-12.5 µg/mL against C. albicans and A. fumigatus). Structure-activity relationship (SAR) analysis revealed that aryl substitution influenced bioactivity, with 4-ethoxy (5h), 2-hydroxy (5f), and 2-fluoro (2a) groups being active, whereas unsubstituted analogues were inactive. These compounds are highlighted as promising antimicrobial leads requiring further in vivo evaluation.
Keyword(s): Benzothiazoles: chemistry (MeSH) ; Benzothiazoles: pharmacology (MeSH) ; Benzothiazoles: chemical synthesis (MeSH) ; Microbial Sensitivity Tests (MeSH) ; Candida albicans: drug effects (MeSH) ; Candida albicans: enzymology (MeSH) ; Molecular Docking Simulation (MeSH) ; Schiff Bases: chemistry (MeSH) ; Schiff Bases: pharmacology (MeSH) ; Schiff Bases: chemical synthesis (MeSH) ; Structure-Activity Relationship (MeSH) ; Benzamides: chemistry (MeSH) ; Benzamides: pharmacology (MeSH) ; Benzamides: chemical synthesis (MeSH) ; Escherichia coli: drug effects (MeSH) ; Escherichia coli: enzymology (MeSH) ; Antifungal Agents: pharmacology (MeSH) ; Antifungal Agents: chemistry (MeSH) ; Antifungal Agents: chemical synthesis (MeSH) ; Sterol 14-Demethylase: metabolism (MeSH) ; Sterol 14-Demethylase: chemistry (MeSH) ; Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing): metabolism (MeSH) ; Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing): antagonists & inhibitors (MeSH) ; Anti-Bacterial Agents: pharmacology (MeSH) ; Anti-Bacterial Agents: chemistry (MeSH) ; Anti-Bacterial Agents: chemical synthesis (MeSH) ; Gram-Positive Bacteria: drug effects (MeSH) ; Gram-Negative Bacteria: drug effects (MeSH) ; Molecular Structure (MeSH) ; antimicrobial activity ; benzamide derivatives ; benzothiazole derivatives ; in silico ADMET ; molecular docking ; Benzothiazoles ; Schiff Bases ; Benzamides ; Antifungal Agents ; Sterol 14-Demethylase ; Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing) ; Anti-Bacterial Agents ; benzothiazole
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