article · ChemistryOpen
A series of chalcone-sulfonamide hybrid compounds, designated 12a to 12h, were synthesised using Claisen-Schmidt condensation with yields ranging between 64% and 83%, verified by nuclear magnetic resonance spectroscopy. Laboratory testing revealed moderate to good antibacterial effects against both Gram-negative organisms, specifically Escherichia coli and Pseudomonas aeruginosa, and Gram-positive organisms, including Staphylococcus aureus and Streptococcus pyogenes. In antioxidant evaluations, the hybrids demonstrated free-radical scavenging activity, with two specific compounds exhibiting the highest potency. Anti-inflammatory testing showed effective protein denaturation inhibition by one derivative, while two others surpassed the reference drug diclofenac sodium in preventing proteinase activity. Computational docking confirmed strong binding affinities to target enzymes involved in bacterial growth and inflammation. In silico profiling further predicted favourable drug-like characteristics, including adherence to Lipinski rules, high gastrointestinal absorption, absence of blood-brain barrier penetration, and low overall toxicity.
Bacterial infections and inflammatory conditions often present overlapping therapeutic challenges, creating a need for versatile treatments. Developing multifunctional small molecules that combine antibacterial, anti-inflammatory, and antioxidant properties could simplify treatment regimens and support future drug development efforts. Identifying molecules with confirmed biological activity and favourable predicted safety profiles helps streamline the earliest stages of therapeutic discovery.
These hybrid molecules represent early-stage chemical leads for pharmaceutical developers seeking multifunctional anti-inflammatory and antibacterial candidates. Because findings are limited to in vitro laboratory assays and computational toxicity predictions, the compounds remain at an early discovery stage, far from clinical use. Substantial further optimisation, in vivo pharmacological validation, and extensive safety trials would be required before industry partners could evaluate them as candidate therapeutics.
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Chalcone‐sulfonamide hybrids ( 12a–h ) were synthesized via Claisen–Schmidt condensation in good yields (64%–83%) and confirmed by NMR spectroscopy. The compounds exhibited moderate to good antibacterial activity against Gram‐negative ( Escherichia coli , Pseudomonas aeruginosa ) and Gram‐positive ( Staphylococcus aureus , Streptococcus pyogenes ) bacteria, with inhibition zones of up to 14.7 mm at 10 mg/mL, lower than that of sulfamethoxazole but comparable to that of related hybrids. DPPH antioxidant evaluation revealed IC 50 values of 5.2–11.8 μg/mL, with compounds 12e and 12c exhibiting the highest activity. Additionally, compound 12e had the strongest protein denaturation inhibition (IC 50 = 29.89 µg/mL), while 12g and 12h showed superior anti‐proteinase activity (IC 50 = 115.6 and 112.2 µg/mL), outperforming diclofenac sodium. Molecular docking against DHPS (1AJ0, 1AD4), myeloperoxidase (1DNU), COX‐2 (5IKR), and topoisomerase IIα (4FM9) showed strong binding affinities (−8.3 to −10.3 kcal/mol), supported by key hydrogen–bonding and hydrophobic interactions. SwissADME and ProTox II analyses indicate favorable drug‐like properties, including Lipinski compliance, high GI absorption, no BBB penetration, and low predicted toxicity (LD 50 > 6000 mg/kg). The hybrids presented here represent promising multifunctional leads with antibacterial, antioxidant, anti‐inflammatory, and drug‐like properties.
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DOI: 10.1002/open.70292
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