Demin Samuël, Van Haver Dirk, Vandewalle Maurits, De Clercq Pierre J, Bouillon Roger, Verstuyf Annemieke
Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, B-9000 Gent, Belgium.
Bioorg Med Chem Lett. 2004 Aug 2;14(15):3885-8. doi: 10.1016/j.bmcl.2004.05.067.
The synthesis and biological activity of novel CD-ring modified analogues of 22-oxa-1alpha,25-dihydroxyvitamin D(3), lacking the D-ring and featuring a connection between C-12 and C-21 (cis-perhydrindane CE-ring analogues), is described. The synthesis of the CE-ring system follows Meyers' methodology for the preparation of enantiomerically pure hydrinden-2-ones. The analogues show a complete lack of binding affinity for the vitamin D receptor (pig nVDR) and of antiproliferative activity (MCF-7 cells), as compared to calcitriol.
描述了新型22-氧杂-1α,25-二羟基维生素D(3)的CD环修饰类似物的合成及其生物活性，这些类似物缺少D环，并在C-12和C-21之间有连接（顺式全氢化茚CE环类似物）。CE环系统的合成遵循迈耶斯制备对映体纯氢化茚-2-酮的方法。与骨化三醇相比，这些类似物对维生素D受体（猪nVDR）完全缺乏结合亲和力，对（MCF-7细胞）也完全没有抗增殖活性。
