Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
Synthesis and evaluation of a 3-position diastereomer of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)
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DOI：
10.1016/j.bmc.2006.07.039
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发表时间：
2006-12-01
影响因子：
3.5
通讯作者：
Kubodera, Noboru
中科院分区：
文献类型：
--
作者：
Hatakeyama, Susurm;Nagashima, Satoshi;Kubodera, Noboru
通过将 A 环片段 (5) 与 C/D 环片段 (6) 偶联的收敛方法合成了 1 α,25-二羟基-2 β-(3-羟基丙氧基) 维生素 D-3 (ED-71, 2)、3-epi-ED-71 (4) 的 3 位非对映异构体。作为 3-epi-ED-71 (4) 的初步体外生物学评价结果，与 ED-71 (2)、1α,25-二羟基维生素 D-3 (1,25(OH)(2)D-3, 1) 相比，牛甲状旁腺细胞中甲状旁腺激素分泌的抑制以及与人重组维生素 D 受体和人维生素 D 结合蛋白的结合亲和力，以及描述了3-epi-1,25(OH)(2)D-3(3)。 (c) 2006 Elsevier Ltd. 保留所有权利。
A 3-position diastereorner of 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy) vitamin D-3 (ED-71, 2), 3-epi-ED-71 (4), was synthesized by the convergent method coupling the A-ring fragment (5) with the C/D-ring fragment (6). As the results of preliminary in vitro biological evaluation of 3-epi-ED-71 (4), the inhibition of parathyroid hormone secretion in bovine parathyroid cells and binding affinity to human recombinant vitamin D receptor and to human vitamin D binding protein in comparison with ED-71 (2), 1 alpha,25-dihydroxyvitamin D-3 (1,25(OH)(2)D-3, 1), and 3-epi-l,25(OH)(2)D-3 (3) are described. (c) 2006 Elsevier Ltd. All rights reserved.