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Fabisiak, Adrian; Brzeminski, Pawel; Berkowska, Klaudia; Rárová, Lucie; Marcinkowska, Ewa; Sicinski, Rafal R.
Bioorganic chemistry, August 2020, 2020-08-00, Letnik: 101Journal Article
Display omitted •Series of 19-norcalcitriol analogs with pegylated 2-alkylidene groups were synthesized.•Pt(II) complexes of two vitamin D analogs were obtained and biologically tested.•Cytotoxic activity of the synthesized 19-norcalcitriol analogs was assessed. 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.
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