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  • Title: Synthesis and biological activities of 26-hydroxy-27-nor-derivatives of 1 alpha, 25-dihydroxyvitamin D3.
    Author: Scheddin D, Mayer H, Wittmann S, Schönecker B, Gliesing S, Reichenbächer M.
    Journal: Steroids; 1996 Oct; 61(10):598-608. PubMed ID: 8910973.
    Abstract:
    Starting with (20S)-20-(p-toluenesulfonyl)oxymethyl-pregna-1, 5-dien-3 alpha-ol (4), we synthesized three vitamin D analogs in 10 to 11 steps: 1 alpha, 26-dihydroxy-27-nor-vitamin D3 (1), its 3-epi analog (2), and 2 beta-methoxy-1 alpha, 26-dihydroxy-27-nor-vitamin D3 (3). We tested the derivatives in the murine mesenchymal cell line C3H1OT1/2. All substances were less potent in inhibition of cell proliferation, inhibition of adipocyte differentiation, and induction of gene activation, and had a lower affinity to the vitamin D receptor than the native vitamin D3 metabolite 1.25(OH)2D3. The affinity of 1 to the vitamin D binding protein was about three times higher than that of 1.25(OH)2D3.
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