Sánchez-Abella Laura, Fernández Susana, Verstuyf Annemieke, Verlinden Lieve, Gotor Vicente, Ferrero Miguel
Departamento de Química Orgánica e Inorgánica and Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, 33006 Oviedo (Asturias), Spain.
Bioorg Med Chem. 2008 Dec 15;16(24):10244-50. doi: 10.1016/j.bmc.2008.10.053. Epub 2008 Oct 26.
Synthesis of two novel 6-s-cis analogues of 1alpha,25-dihydroxyvitamin D3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2beta-(3'-hydroxypropoxy) moiety or a 2beta,3beta-epoxy group into 1alpha,25-OH(2)-19-nor-pre-D3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation.
描述了使用莽草酸及其4-表异构体作为通用手性起始原料合成两种新型的1α,25-二羟基维生素D3的6-s-顺式类似物。这些衍生物在1α,25-OH(2)-19-去甲前维生素D3中含有一个2β-(3'-羟基丙氧基)部分或一个2β,3β-环氧基团。发现合成的类似物不适合与维生素D受体结合，并且对维生素D结合蛋白显示出较弱的结合亲和力。新衍生物未能抑制细胞增殖。
