Novel preparation of substituted oxazolines condensed to d-ring of estrane skeleton and characterization of their antiproliferative properties

Kiss, Anita and Jójárt, Rebeka and Mernyák, Erzsébet and Bartha, Sándor and Minorics, Renáta and Zupkó, István and Schneider, Gyula (2021) Novel preparation of substituted oxazolines condensed to d-ring of estrane skeleton and characterization of their antiproliferative properties. STEROIDS. ISSN 0039-128X (In Press)

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Abstract

A simple and efficient synthesis of novel estrone 16α,17α-oxazoline derivatives substituted at the D ring (compounds 6a-g) is described. The reduction of 16α-azido-3-methoxyestra-1,3,5- trien-17-one (1) in methanol in the presence of CeCl3 under the condition of the Luche reaction produced two epimeric azido alcohol (16α-azido-17α-hydroxy and 16α-azido-17β- hydroxy) azidoalkohol derivtives derivatives of estra-1,3,5(10)-triene-3-methyl ether (compounds 2 and 3) in a yield of 90% and 7.6%. The reaction of the sterically unhindered 16α-azido-17α-hydroxy-estra-1,3,5(10)-triene-3-methyl ether (2) ( 2) with a range of benzaldehydes under the condition of the Schmidt rearrangement yielded D-ring substituted estrone 16α,17α-oxazoline derivatives (6a-g). 6a-g. The in vitro antiproliferative activities of compounds 2,3 1, 2, 6a-g were also determined by means of MTT assays on a panel of human cancer cell lines HeLa, SiHa, C-33 A, A2780, MCF-7, MDA-MB-231 and T47D.

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