Efficient and Versatile Synthesis of Novel 2α-Substituted 1α,25-Dihydroxyvitamin D3 Analogues and Their Docking to Vitamin D Receptors
- 27 November 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (26) , 8760-8771
- https://doi.org/10.1021/jo010375i
Abstract
Novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues with 2α-alkyl and 2α-hydroxyalkyl groups were systematically synthesized from d-xylose. Their conformation on binding to the ligand binding domain (LBD) of the vitamin D receptor was analyzed. It has been found that the 2α-hydroxypropyl group best fits the cavity of the LBD, and the binding activity is three times higher than that for the natural hormone.Keywords
This publication has 17 references indexed in Scilit:
- Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analoguesBioorganic & Medicinal Chemistry Letters, 2000
- Novel nonsecosteroidal vitamin D mimics exert VDR-modulating activities with less calcium mobilization than 1,25-dihydroxyvitamin D3Chemistry & Biology, 1999
- Convergence of Transforming Growth Factor-β and Vitamin D Signaling Pathways on SMAD Transcriptional CoactivatorsScience, 1999
- Synthesis and biological activity of 2-methyl-20-epi analogues of 1α,25-dihydroxyvitamin D3Bioorganic & Medicinal Chemistry Letters, 1998
- A novel and practical route to A-ring enyne synthon for 1α,25-dihydroxyvitamin D3 analogs: Synthesis of A-ring diastereomers of 1α,25-dihydroxyvitamin D3 and 2-methyl-1,25-dihydroxyvitamin D3Bioorganic & Medicinal Chemistry Letters, 1998
- Synthesis of Vitamin D (Calciferol)Chemical Reviews, 1995
- Synthetic Approaches to Vitamin DSynthesis, 1994
- New strategies for the synthesis of vitamin D metabolites via palladium-catalyzed reactionsJournal of the American Chemical Society, 1992
- Direct repeats as selective response elements for the thyroid hormone, retinoic acid, and vitamin D3 receptorsCell, 1991
- Regulatory activities of 2β-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D3, a novel synthetic vitamin D3 derivative, on calcium metabolismBiochemical and Biophysical Research Communications, 1989