Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series.

Dóra Kovács, Zalán Kádár, Gergő Mótyán, Gyula Schneider, János Wölfling, István Zupkó, Eva Frank

Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.

Steroids 2012 Sep

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Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17α-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Δ(16,17)exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780). Copyright © 2012 Elsevier Inc. All rights reserved.

Citation

Dóra Kovács, Zalán Kádár, Gergő Mótyán, Gyula Schneider, János Wölfling, István Zupkó, Eva Frank. Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series. Steroids. 2012 Sep;77(11):1075-85