{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:58:15Z","timestamp":1787029095751,"version":"build-2736575974"},"reference-count":65,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2024,1,11]],"date-time":"2024-01-11T00:00:00Z","timestamp":1704931200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003549","name":"Hungarian Scientific Research Fund","doi-asserted-by":"publisher","award":["OTKA K_129037"],"award-info":[{"award-number":["OTKA K_129037"]}],"id":[{"id":"10.13039\/501100003549","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003549","name":"Hungarian Scientific Research Fund","doi-asserted-by":"publisher","award":["TKP2021-EGA-32"],"award-info":[{"award-number":["TKP2021-EGA-32"]}],"id":[{"id":"10.13039\/501100003549","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund","award":["OTKA K_129037"],"award-info":[{"award-number":["OTKA K_129037"]}]},{"name":"Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund","award":["TKP2021-EGA-32"],"award-info":[{"award-number":["TKP2021-EGA-32"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of novel triazole-tethered ferrocenoylamino-substituted cinchona\u2013chalcone hybrids along with two representative benzoylamino-substituted reference compounds were prepared by three methods of CuAAC chemistry. In line with the limited success or complete failure of attempted conversions with low catalyst loadings, by means of DFT modeling studies, we demonstrated that a substantial part of the Cu(I) ions can be chelated and thus trapped in the aroylamino-substituted cinchona fragment and all of the accessible coordinating sites of the chalcone residues. Accordingly, increased amounts of catalysts were used to achieve acceptable yields; however, the cycloadditions with para-azidochalcones were accompanied by partial or complete aldehyde-forming hydrolytic fission of the enone C=C bond in a substituent-, solvent- and copper load-dependent manner. The experienced hydrolytic stability of the hybrids obtained by cycloadditions with ortho-azidochalcones was interpreted in terms of relative energetics, DFT reactivity indices and MO analysis of simplified models of two isomer copper\u2013enone complexes. The novel hybrids were evaluated on HeLa, MDA-MB-231 and A2780 cell lines and showed substantial activity at low-to-submicromolar concentrations. An organometallic model carrying 3,4,5-trimethoxyphenyl residue in the enone part with a para-disubstituted benzene ring in the central skeletal region was identified as the most potent antiproliferative lead, characterized by submicromolar IC50 values measured on the three investigated cells. The biological assays also disclosed that this ferrocenoylamino-containing lead compound displays a ca. two- to five-fold more substantial antiproliferative effect than its benzoylamino-substituted counterpart.<\/jats:p>","DOI":"10.3390\/molecules29020375","type":"journal-article","created":{"date-parts":[[2024,1,11]],"date-time":"2024-01-11T12:56:33Z","timestamp":1704977793000},"page":"375","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["CuAAC-Based Synthesis, Copper-Catalyzed Aldehyde-Forming Hydrolytic Fission and Antiproliferative Evaluation of Novel Ferrocenoylamino-Substituted Triazole-Tethered Quinine\u2013Chalcone Hybrids"],"prefix":"10.3390","volume":"29","author":[{"given":"Ant\u00f3nio","family":"Dembo","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University (ELTE), P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"},{"name":"Hevesy Gy\u00f6rgy PhD School of Chemistry, P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Etelka","family":"Ferenczi","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University (ELTE), P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"},{"name":"Hevesy Gy\u00f6rgy PhD School of Chemistry, P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4990-4281","authenticated-orcid":false,"given":"Tam\u00e1s","family":"Jernei","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University (ELTE), P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Bor","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, E\u00f6tv\u00f6s u. 6., H-6720 Szeged, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8519-4830","authenticated-orcid":false,"given":"Zsuzsanna","family":"Schelz","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, E\u00f6tv\u00f6s u. 6., H-6720 Szeged, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3243-5300","authenticated-orcid":false,"given":"Istv\u00e1n","family":"Zupk\u00f3","sequence":"additional","affiliation":[{"name":"Institute of Pharmacodynamics and Biopharmacy, University of Szeged, E\u00f6tv\u00f6s u. 6., H-6720 Szeged, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9611-5168","authenticated-orcid":false,"given":"Szil\u00e1rd","family":"Varga","sequence":"additional","affiliation":[{"name":"HUN-REN Research Centre for Natural Sciences, Institute of Organic Chemistry, Magyar Tud\u00f3sok Krt 2., H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2107-7309","authenticated-orcid":false,"given":"Antal","family":"Cs\u00e1mpai","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry, E\u00f6tv\u00f6s Lor\u00e1nd University (ELTE), P\u00e1zm\u00e1ny P. s\u00e9t\u00e1ny 1\/A, H-1117 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"17","DOI":"10.3322\/caac.21763","article-title":"Cancer Statistics, 2023","volume":"73","author":"Siegel","year":"2023","journal-title":"CA Cancer J. 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