Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary.
Steroids. 2012 Sep;77(11):1075-85. doi: 10.1016/j.steroids.2012.05.003. Epub 2012 May 18.
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).
不同芳基腈氧化物与美雌醇的区域选择性 1,3-偶极环加成反应以良好至优秀的收率得到了新型甾体 17α-异噁唑。发现铜 (I) 是一种有效的催化剂，可加速分子间环闭合，并且仅得到 3,5-取代的异噁唑。然而，环加成产物的产率受到 1,3-二极体芳基部分取代基的影响。此外，初级产物的脱水导致相应的 Δ(16,17)外消旋杂环衍生物。所有合成的化合物都进行了体外药理学研究，以评估它们相对于三种人恶性细胞系（HeLa、MCF7 和 A2780）的抗增殖作用。
