{
  "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.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland",
    "Doctoral School of Exact and Natural Sciences, University of Lodz, Jana Matejki 21/23, 90-237 Lodz, Poland",
    "Department of Oncobiology and Epigenetics, Institute of Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, Pomorska 141/143, 90-236 Lodz, Poland",
    "Higher Education and Industrial Cooperation Centre, University of Miskolc, Miskolc-Egyetemváros, 3515 Miskolc, Hungary",
    "Department of the Chemistry of Cosmetic Raw Materials, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland",
    "Department of Medical Chemistry, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 9,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Patryk Czapnik",
      "orcid": "0000-0002-7460-0864"
    },
    {
      "affs": [
        0
      ],
      "name": "Magdalena Małecka",
      "orcid": "0000-0003-3384-9855"
    },
    {
      "affs": [
        2
      ],
      "name": "Pawel Hikisz"
    },
    {
      "affs": [
        0
      ],
      "name": "Adam Buczkowski",
      "orcid": "0000-0001-9026-5202"
    },
    {
      "affs": [
        0
      ],
      "name": "Artur Stepniak",
      "orcid": "0000-0002-2407-1298"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Khalida Khalil"
    },
    {
      "affs": [
        3
      ],
      "name": "Rehana Bano"
    },
    {
      "affs": [
        4
      ],
      "name": "Elzbieta Budzisz",
      "orcid": "0000-0001-9949-8723"
    },
    {
      "affs": [
        5
      ],
      "name": "Angelika A. Adamus-Grabicka",
      "orcid": "0000-0003-0119-599X"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/2r5521tm2an4m.bib",
  "cited_by": 0,
  "doi": "10.3390/molecules31213990",
  "fulltext_url": null,
  "id": "2r5521tm2an4m",
  "issns": [
    "1420-3049"
  ],
  "landing_url": "https://www.mdpi.com/1420-3049/31/21/3990",
  "language": null,
  "licence": "CC-BY-4.0",
  "licence_label": "CC BY 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [],
  "openalex": null,
  "pdf_url": null,
  "pmcid": null,
  "pmid": null,
  "published": "2026-11-05",
  "publisher": "MDPI AG",
  "ris": "https://research.draconitic.com/paper/2r5521tm2an4m.ris",
  "sources": [
    {
      "first_seen": "2026-11-06T00:21:09Z",
      "native_id": "10.3390/molecules31213990",
      "source": "crossref",
      "url": "https://www.mdpi.com/1420-3049/31/21/3990"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "issn:1420-3049",
      "subfield": "general"
    }
  ],
  "title": "New Chromone Analogues as Potential Bioactive Compounds: Cyclodextrin Complexation and Molecular Docking",
  "title_text": "New Chromone Analogues as Potential Bioactive Compounds: Cyclodextrin Complexation and Molecular Docking",
  "type": "peer-reviewed",
  "updated_at": "2026-11-07T00:21:07Z",
  "url": "https://research.draconitic.com/paper/2r5521tm2an4m",
  "venue": "Molecules",
  "versions": []
}