Synthesis, Biological Evaluation, Molecular Docking and DFT Studies of Electronically Tuned Benzylidene-Based Schiff Bases
8 affiliations
- 1Department of Pharmaceutical Chemistry, Hamidiye Faculty of Pharmacy, University of Health Sciences, Istanbul 34668, Turkey
- 2Experimental Medicine Application & Research Center, Validebağ Research Park, University of Health Sciences, Istanbul 34662, Turkey
- 3Department of Pharmaceutical Chemistry, Institute of Graduate Studies in Health Sciences, Istanbul University, Istanbul 34116, Turkey
- 4Opticianry Program, Hamidiye Vocational School of Health Services, University of Health Sciences, Istanbul 34668, Turkey
- 5Department of Pharmaceutical Microbiology, Hamidiye Faculty of Pharmacy, University of Health Sciences, Istanbul 34668, Turkey
- 6Department of Phytotherapy, Hamidiye Institute of Health Sciences, University of Health Sciences, Istanbul 34668, Turkey
- 7Department of Biostatistics and Medical Informatics, Faculty of Medicine, İstinye University, Istanbul 34396, Turkey
- 8Department of Biology, Science Faculty, Selcuk University, Konya 42130, Turkey
Abstract
Inspired by the medicinally relevant stilbene scaffold, a series of six electronically tuned benzylidene-based Schiff base derivatives were designed, synthesized, and characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS analyses. The biological properties of the synthesized compounds were investigated through antioxidant, enzyme inhibitory, and antimicrobial assays, while molecular docking and density functional theory (DFT) calculations were performed to rationalize the experimental findings and structure-activity relationships. Compounds 3 and 6 exhibited the strongest antioxidant activities, particularly in ABTS, CUPRAC, FRAP, phosphomolybdenum, and metal-chelating assays. Compounds 1–3 and 5 demonstrated measurable α-glucosidase inhibitory activity, although they were less potent than acarbose, whereas compounds 1 and 2 showed the highest tyrosinase inhibition within the synthesized series. Antimicrobial evaluation revealed moderate activity across the series, with compound 3 displaying relatively higher antimicrobial activity within the synthesized series. Docking studies demonstrated favorable interactions within enzyme active sites, while DFT calculations provided insights into electronic properties and molecular reactivity. As a result, the investigated substitution patterns were associated with differences in biological activity within the synthesized series, with compound 3 showing relatively favorable activity in selected assays and warranting further investigation.
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BibTeX
@article{buran2026synthesis,
title = {{Synthesis, Biological Evaluation, Molecular Docking and DFT Studies of Electronically Tuned Benzylidene-Based Schiff Bases}},
author = {Kerem Buran and Elmas Rumeysa Yıldırım and Nazmiye Öner and Derya Doğanay and Esra Mertoğlu and Abdullahi İbrahim Uba and Gokhan Zengin},
journal = {Molecules (Basel, Switzerland)},
year = {2026},
month = oct,
doi = {10.3390/molecules31193519},
url = {https://europepmc.org/article/PMC/PMC13666581},
note = {CC BY},
}
RIS
TY - JOUR
TI - Synthesis, Biological Evaluation, Molecular Docking and DFT Studies of Electronically Tuned Benzylidene-Based Schiff Bases
AU - Kerem Buran
AU - Elmas Rumeysa Yıldırım
AU - Nazmiye Öner
AU - Derya Doğanay
AU - Esra Mertoğlu
AU - Abdullahi İbrahim Uba
AU - Gokhan Zengin
PY - 2026
DA - 2026/10/01
JO - Molecules (Basel, Switzerland)
DO - 10.3390/molecules31193519
UR - https://europepmc.org/article/PMC/PMC13666581
AB - Inspired by the medicinally relevant stilbene scaffold, a series of six electronically tuned benzylidene-based Schiff base derivatives were designed, synthesized, and characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS analyses. The biological properties of the synthesized compounds were investigated through antioxidant, enzyme inhibitory, and antimicrobial assays, while molecular docking and density functional theory (DFT) calculations were performed to rationalize the experimental findings and structure-activity relationships. Compounds 3 and 6 exhibited the strongest antioxidant activities, particularly in ABTS, CUPRAC, FRAP, phosphomolybdenum, and metal-chelating assays. Compounds 1–3 and 5 demonstrated measurable α-glucosidase inhibitory activity, although they were less potent than acarbose, whereas compounds 1 and 2 showed the highest tyrosinase inhibition within the synthesized series. Antimicrobial evaluation revealed moderate activity across the series, with compound 3 displaying relatively higher antimicrobial activity within the synthesized series. Docking studies demonstrated favorable interactions within enzyme active sites, while DFT calculations provided insights into electronic properties and molecular reactivity. As a result, the investigated substitution patterns were associated with differences in biological activity within the synthesized series, with compound 3 showing relatively favorable activity in selected assays and warranting further investigation.
SN - 1420-3049
ER -