New Chromone Analogues as Potential Bioactive Compounds: Cyclodextrin Complexation and Molecular Docking
6 affiliations
- 1Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland
- 2Doctoral School of Exact and Natural Sciences, University of Lodz, Jana Matejki 21/23, 90-237 Lodz, Poland
- 3Department of Oncobiology and Epigenetics, Institute of Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, Pomorska 141/143, 90-236 Lodz, Poland
- 4Higher Education and Industrial Cooperation Centre, University of Miskolc, Miskolc-Egyetemváros, 3515 Miskolc, Hungary
- 5Department of the Chemistry of Cosmetic Raw Materials, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland
- 6Department of Medical Chemistry, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland
Abstract
Chromone is an important structural motif in numerous biologically active natural and synthetic compounds. The aim of the present study is to synthesize and characterize a series of novel chromone derivatives bearing imidazole and pyrazole moieties. The synthesis involved a two-step procedure in which methyl 3-chromonecarboxylate derivatives were prepared and then condensed with imidazole and pyrazole analogues. The structures of the compounds were characterized using spectroscopy, single-crystal X-ray diffraction and Hirshfeld surface analysis. Compounds 1 and 1A were subjected to ITC titration in DMSO. Anticancer potential of synthetized substances was evaluated against three breast cancer cell lines (MCF-7, MDA-MB-231 and HCC38), and two endometrial cancer cell lines (Ishikawa and Hec-1-A). Compounds 1B and 1C, bearing 3-(1H-imidazol-1-yl)propan-1-amine and3-(3,5-dimethyl-4H-pyrazol-4-yl)propan-1-amine moieties, respectively, exhibited the most pronounced, albeit modest, cytotoxic activity against MCF-7 cells, with IC50 values of approximately 80 μM. In HMEC-1 human microvascular endothelial cells (used as a non-cancerous reference model), the same compounds lowered the signal of the dihydroethidium (DHE) probe, suggesting a modest antioxidant effect; these redox results are reported separately from the anticancer assays. The compounds were subjected to further complex analysis using 2′,7′-dichlorodihydrofluorescein diacetate (H2DCFDA) and molecular docking studies. This complex approach provided a qualitative insight into the structure–activity relationships of the studied derivatives. Given the modest cytotoxicity and limited selectivity of Compounds 1B and 1C, together with their redox-modulating effect observed in HMEC-1 cells, these compounds should be regarded as a starting point for further investigation rather than as promising anticancer candidates.
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BibTeX
@article{czapnik2026chromone,
title = {{New Chromone Analogues as Potential Bioactive Compounds: Cyclodextrin Complexation and Molecular Docking}},
author = {Patryk Czapnik and Magdalena Małecka and Pawel Hikisz and Adam Buczkowski and Artur Stepniak and Khalida Khalil and Rehana Bano and Elzbieta Budzisz and Angelika A. Adamus-Grabicka},
journal = {Molecules},
year = {2026},
month = nov,
doi = {10.3390/molecules31213990},
url = {https://www.mdpi.com/1420-3049/31/21/3990},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - New Chromone Analogues as Potential Bioactive Compounds: Cyclodextrin Complexation and Molecular Docking
AU - Patryk Czapnik
AU - Magdalena Małecka
AU - Pawel Hikisz
AU - Adam Buczkowski
AU - Artur Stepniak
AU - Khalida Khalil
AU - Rehana Bano
AU - Elzbieta Budzisz
AU - Angelika A. Adamus-Grabicka
PY - 2026
DA - 2026/11/05
JO - Molecules
DO - 10.3390/molecules31213990
UR - https://www.mdpi.com/1420-3049/31/21/3990
AB - Chromone is an important structural motif in numerous biologically active natural and synthetic compounds. The aim of the present study is to synthesize and characterize a series of novel chromone derivatives bearing imidazole and pyrazole moieties. The synthesis involved a two-step procedure in which methyl 3-chromonecarboxylate derivatives were prepared and then condensed with imidazole and pyrazole analogues. The structures of the compounds were characterized using spectroscopy, single-crystal X-ray diffraction and Hirshfeld surface analysis. Compounds 1 and 1A were subjected to ITC titration in DMSO. Anticancer potential of synthetized substances was evaluated against three breast cancer cell lines (MCF-7, MDA-MB-231 and HCC38), and two endometrial cancer cell lines (Ishikawa and Hec-1-A). Compounds 1B and 1C, bearing 3-(1H-imidazol-1-yl)propan-1-amine and3-(3,5-dimethyl-4H-pyrazol-4-yl)propan-1-amine moieties, respectively, exhibited the most pronounced, albeit modest, cytotoxic activity against MCF-7 cells, with IC50 values of approximately 80 μM. In HMEC-1 human microvascular endothelial cells (used as a non-cancerous reference model), the same compounds lowered the signal of the dihydroethidium (DHE) probe, suggesting a modest antioxidant effect; these redox results are reported separately from the anticancer assays. The compounds were subjected to further complex analysis using 2′,7′-dichlorodihydrofluorescein diacetate (H2DCFDA) and molecular docking studies. This complex approach provided a qualitative insight into the structure–activity relationships of the studied derivatives. Given the modest cytotoxicity and limited selectivity of Compounds 1B and 1C, together with their redox-modulating effect observed in HMEC-1 cells, these compounds should be regarded as a starting point for further investigation rather than as promising anticancer candidates.
SN - 1420-3049
ER -