Synthesis of 19-norcalcitriol analogs with alkylidene moieties at C-2 based on succinic acid and L-methionine

Publication date: Available online 26 July 2017
Source:The Journal of Steroid Biochemistry and Molecular Biology
Author(s): Adrian Fabisiak, Pawel Brzeminski, Klaudia Berkowska, Ewa Marcinkowska, Rafal R. Sicinski
On the basis of the literature data, our previous research work and docking experiments, we designed novel 19-norvitamin D compounds having elongated 2-alkylidene substituents. These 19-norcalcitriol derivatives have attached 2-(3′-aminopropylidene) substituent in which the nitrogen atom bears acyl residue derived from succinic acid and L-methionine. Both compounds were obtained by the same synthetic strategy involving Julia coupling of the A-ring ketone with the known C/D-ring sulfone. In the obtained 1α,25-dihydroxy-19-norvitamin D3 derivative, the alkylidene substituent at C-2 was further elaborated to the desired structures.

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