Synthesis, spectroscopic characterization, biological activities, and molecular docking studies of novel furan-based azo- and ester-functionalized chalcone derivatives
Journal of the Indian Chemical Society, cilt.103, sa.8, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 103 Sayı: 8
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.jics.2026.102878
- Dergi Adı: Journal of the Indian Chemical Society
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, EMBASE
- Anahtar Kelimeler: Antimicrobial, Antioxidant, Biofilm inhibition, Cell viability, DNA cleavage
- Yıldız Teknik Üniversitesi Adresli: Evet
Özet
Two structurally related furan-based chalcone derivatives F AZO bearing an azo linkage and F EST containing an ester moiety have been presented. The incorporation of azo and ester groups aimed to improve electronic delocalization, target binding affinity, and biological efficacy. The chemical structures of the synthesized chalcone/azo and chalcone/ester derivatives were confirmed by classical spectroscopic methods such as proton nuclear magnetic resonance spectroscopy (1H NMR), carbon-13 attached proton test nuclear magnetic resonance spectroscopy (13C(APT)-NMR), Fourier-Transform Infrared Spectroscopy (FT-IR), and High Resolution-Mass Spectrometry (HR-MS). F AZO and F EST demonstrated moderate antioxidant activity, exhibiting 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging efficiencies of 37.02% and 34.01%, respectively. Both compounds effectively inhibited amylase, particularly at 100 mg/L, suggesting their potential as antidiabetic agents. F AZO and F EST induced complete Deoxyribonucleic acid (DNA) cleavage at concentrations of 50, 100, and 200 mg/L. Both compounds showed the highest antimicrobial activity against Enterococcus faecalis ( E. faecalis ) and Candida albicans ( C. albicans ) among the tested microorganisms. At 200 mg/L, F AZO inhibited Staphylococcus aureus ( S. Aureus ) biofilm formation as 64.11%, whereas F EST showed 63.59% inhibition. At the same concentration, F AZO and F EST inhibited Pseudomonas aeruginosa ( P. Aeruginosa ) biofilm by 71.65% and 78.52%, respectively. F AZO and F EST demonstrated superior microbial cell viability inhibition capabilities as 98.12% and 100% against Escherichia coli ( E. coli ) under dark conditions at 200 mg/L, respectively, and they displayed photodynamic antimicrobial abilities (PDaT) against E. coli as 94.66% and 100% inhibition at 100 mg/L and also 100% and 100% inhibition, respectively. Based on the results of molecular docking study, −8.33 and −6.84 kcal/mol were found for the strength of interactions for F AZO and F EST ligands towards the α-amylase target and −12.43 and −9.87 kcal/mol were found for their strengths towards the DNA target revealing them as potential inhibitors. These values highlight the various potential applications of F AZO and F EST in biomedical industries.