Stereocontrolled Synthesis of the Four Possible 3-Methoxy and 3-Benzyloxy-16-Triazolyl-methyl-estra-17-ol Hybrids and their Antiproliferative Activities

Publication date: Available online 16 September 2019Source: SteroidsAuthor(s): Anita Kiss, János Wölfling, Erzsébet Mernyák, Éva Frank, Zsanett Benke, Seyyed Ashkan Senobar Tahaei, István Zupkó, Sándor Mahó, Gyula SchneiderAbstractThe four possible isomers of each of 3-methoxy- and 3-benzyloxyestra-1,3,5(10)-trien-17-ols (5–8 and 9–12) were converted through 16-p-tosyloxymethyl- or 16-bromomethyl derivatives into their 3-methoxy- and 3-benzyloxy-16-azidomethylestra(1,3,5(10)-triene derivatives (13–16 and 17–20). The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of these compounds with different terminal alkynes afforded novel 1,4-disubstituted diastereomers (21a–f, 22a–f, 23a–f, 24a–f and 25a–f, 26a–f, 27a–f, 28a-f). The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on four malignant human cell lines of gynecological origin (Hela, SiHa, MCF-7 and MDA-MB-231).Graphical abstract
Source: Steroids - Category: Drugs & Pharmacology Source Type: research