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Turkish Journal of Chemistry

Abstract

Quinoline derivatives have garnered significant attention owing to their wide range of biological activities, particularly their anticancer potential. In this study, six novel 4-aminoquinoline derivatives incorporating a phenylalanine methyl ester moiety were synthesized and structurally characterized. The cytotoxic activities of the synthesized compounds were assessed against A549 and MCF-7 cancer cell lines, along with the noncancerous NIH3T3 fibroblast cell line. Compounds 4d and 4e displayed potent anticancer activity with low IC₅₀ values, while exhibiting negligible toxicity toward normal cells. Moreover, these compounds exhibited moderate inhibitory activity against EGFR. Molecular docking studies were conducted to elucidate the binding modes of compounds 4d and 4e at the EGFR active site. To better elucidate their electronic structures and reactivity profiles, density functional theory (DFT) calculations were carried out to determine frontier molecular orbital energies, global reactivity descriptors, dipole moments, and molecular electrostatic potential (MEP) maps. Theoretical data were correlated with the experimental biological activities, revealing consistent trends, particularly among the most active compounds. Furthermore, theoretical NMR chemical shift calculations were performed for the synthesized compounds.

Author ORCID Identifier

İLBİLGE MERVE ŞENOL: 0000-0003-4155-4424

BEGÜM NURPELİN SAĞLIK ÖZKAN: 0000-0002-0151-6266

İLHAMİ ÇELİK: 0000-0002-5384-4755

AHMET KARABURUN: 0000-0002-2503-3824

DOI

10.55730/1300-0527.3758

Keywords

4-aminoquinoline, A549 cytotoxicity, MCF-7 cytotoxicity, EGFR inhibition, DFT analysis

First Page

616

Last Page

631

Publisher

The Scientific and Technological Research Council of Türkiye (TÜBİTAK)

Creative Commons License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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