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Design, synthesis and biological evaluation of novel 2-alkylidene 19-norcalcitriol analogs
A. Fabisiak, P. Brzeminski, K. Berkowska, L. Rárová, E. Marcinkowska, RR. Sicinski
Language English Country United States
Document type Journal Article, Research Support, Non-U.S. Gov't
- MeSH
- HL-60 Cells MeSH
- Calcitriol chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Ligands MeSH
- MCF-7 Cells MeSH
- Drug Evaluation, Preclinical MeSH
- Antineoplastic Agents pharmacology MeSH
- Drug Design * MeSH
- Receptors, Calcitriol drug effects MeSH
- Drug Screening Assays, Antitumor MeSH
- Molecular Docking Simulation MeSH
- Binding Sites MeSH
- Cell Survival drug effects MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
Continuing our studies aimed at A-ring modified vitamin D compounds, we designed novel 19-norcalcitriol derivatives bearing at C-2 pegylated chains of different lengths. The terminal fragments of these substituents contain hydroxyls or moieties possessing nitrogen and/or sulfur atoms capable of transition metal ions complexation. Also, two conjugate-type platinum(II) complexes of 19-norcalcitriol were obtained in which l-methionine served as chelating moiety. The convergent synthesis of the target 19-norcalcitriol analogs involved several steps with the crucial one being condensation of A-ring phosphine oxide and the known Grundmann ketone by Wittig-Horner reaction. Further elaboration of the 2-alkylidene substituent provided all final compounds which were then tested to determine their affinity for the vitamin D receptor and cytotoxic activity.
Department of Biotechnology University of Wroclaw Joliot Curie 14a 50 383 Wroclaw Poland
Department of Chemistry University of Warsaw Pasteura 1 02 093 Warsaw Poland
References provided by Crossref.org
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