Synthesis, Structure and In Vitro Cytotoxic Activity of Novel Cinchona-Chalcone Hybrids with 1,4-Disubstituted- and 1,5-Disubstituted 1,2,3-Triazole Linkers.
Antineoplastic Agents
/ chemistry
Cell Line, Tumor
Cell Proliferation
/ drug effects
Chalcone
/ chemical synthesis
Chemistry Techniques, Synthetic
Cinchona
/ chemistry
Humans
Inhibitory Concentration 50
Models, Molecular
Molecular Conformation
Molecular Structure
Structure-Activity Relationship
Triazoles
/ chemistry
1,2,3-triazole
cell cycle analysis
chalcone
cinchona
cytotoxicity
hybrid compounds
structure-activity relationships
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
11 Nov 2019
11 Nov 2019
Historique:
received:
25
10
2019
revised:
06
11
2019
accepted:
06
11
2019
entrez:
14
11
2019
pubmed:
14
11
2019
medline:
9
4
2020
Statut:
epublish
Résumé
By means of copper(I)-and ruthenium(II)-catalyzed click reactions of quinine- and quinidine-derived alkynes with azide-substituted chalcones a systematic series of novel cinchona-chalcone hybrid compounds, containing 1,4-disubstituted- and 1,5-disubstituted 1,2,3-triazole linkers, were synthesized and evaluated for their cytotoxic activity on four human malignant cell lines (PANC-1, COLO-205, A2058 and EBC-1). In most cases, the cyclization reactions were accompanied by the transition-metal-catalyzed epimerization of the C9-stereogenic centre in the cinchona fragment. The results of the in vitro assays disclosed that all the prepared hybrids exhibit marked cytotoxicity in concentrations of low micromolar range, while the C9-epimerized model comprising quinidine- and (
Identifiants
pubmed: 31718009
pii: molecules24224077
doi: 10.3390/molecules24224077
pmc: PMC6891474
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Triazoles
0
Chalcone
5S5A2Q39HX
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Hungarian Scientific Research Fund
ID : 129037
Organisme : Nemzeti Kutatási Fejlesztési és Innovációs Hivatal
ID : 16-1-2016-0036
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
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