Synthesis of 23,23-Difluoro-24-nor- and 24′,24′-Difluoro-24-Homovitamin D3 Analogues and Unexpected Structure-Activity Relationships

References (27)

1. 1 Sakaki, 2000, Dual metabolic pathway of 25-hydroxyvitamin D3 catalyzed by human CYP24 [DOI]
2. 2 Yasuda, 2021, Elucidation of metabolic pathways of 25-hydroxyvitamin D3 mediated by Cyp24A1 and Cyp3A using Cyp24a1 knockout rats generated by CRISPR/Cas9 system [DOI]
3. 3 Kawagoe, F., Mototani, S., and Kittaka, A. (2021). Design and synthesis of fluoro analogues of vitamin D. Int. J. Mol. Sci., 22. [DOI]
4. 4 Maestro, 2019, Vitamin D and its synthetic analogs [DOI]
5. 5 Kobayashi, 1982, Studies on organic fluorine compounds. XXXIX. Studies on steroids. LXXIX. Synthesis of 1α,25-dihydroxy-26,26,26,27,27,27-hexafluorovitamin D3 [DOI]
6. 6 Kawagoe, 2018, Recent developments for introducing a hexafluoroisopropanol unit into the vitamin D side chain [DOI]
7. 7 Morii, 1998, Falecalcitriol phase secondary hyperparathyroidism treatment study group III. Efficacy and safety of oral falecalcitriol in reducing parathyroid hormone in hemodialysis patients with secondary hyperparathyroidism [DOI]
8. 8 Bikle, 2014, Vitamin D Metabolism, Mechanism of Action, and Clinical Applications [DOI]
9. 9 Yamada, 1979, Synthesis of 24,24-difluoro-25-hydroxyvitamin D3 [DOI]
10. 10 Kobayashi, 1979, Synthesis of 24,24-difluoro- and 24ξ-fluoro-25-hydroxyvitamin D3 [DOI]
11. 11 Shiuey, 1988, Triply convergent synthesis of 1α,25-dihydroxy-24(R)-fluorocholecalciferol [DOI]
12. 12 Kawagoe, F., Mototani, S., Yasuda, K., Mano, H., Sakaki, T., and Kittaka, A. (2021). Stereoselective synthesis of 24-fluoro-25-hydroxyvitamin D3 analogues and their stability to hCYP24A1-dependent catabolism. Int. J. Mol. Sci., 22. [DOI]
13. 13 Shiuey, S.-J., Partridge, J.J., Chadha, N.K., Boris, A., and Uskoković, M.R. (1985). Stereospecific synthesis of 1α,25-dihydroxy-24R-fluorocholecalciferol (Ro23-0233). Vitamin D, Chemical, Biochemical and Clinical Update, Walter de Gruyter.
14. 14 Kawagoe, 2019, Introduction of fluorine atoms to vitamin D3 side-chain and synthesis of 24,24-difluoro-25-hydroxyvitamin D3 [DOI]
15. 15 Kawagoe, 2025, Side-chain fluorine engineering of vitamin D3 derivatives for VDR-silent SREBP inhibitors [DOI]
16. 16 Plum, 2004, Biologically active noncalcemic analogs of 1α,25-dihydroxyvitamin D with an abbreviated side chain containing no hydroxyl [DOI]
17. 17 Toh, 1983, Studies on a convergent route to side-chain analogues of vitamin D: 25-hydroxy-23-oxavitamin D3 [DOI]
18. 18 Mototani, S., Kawagoe, F., Yasuda, K., Mano, H., Sakaki, T., and Kittaka, A. (2022). The first convergent synthesis of 23,23-difluoro-25-hydroxyvitamin D3 and its 24-hydroxy derivatives: Preliminary assessment of biological activities. Molecules, 27. [DOI]
19. 19 Grzywacz, 2007, Methyl substitution of the 25-hydroxy group on 2-methylene-19-nor-1α,25-dihydroxyvitamin D3 (2MD) reduces potency but allows bone selectivity [DOI]
20. 20 Nakamura, 1981, New acyl anion equivalent. A short route to the enol lactam intermediate in cytochalasin synthesis [DOI]
21. 21 Mano, 2018, Development of a highly sensitive in vitro system to detect and discriminate between vitamin D receptor agonists and antagonists based on split-luciferase technique [DOI]
22. 22 Kusudo, 2004, Metabolism of A-ring diastereomers of 1α,25-dihydroxyvitamin D3 by CYP24A1 [DOI]
23. 23 Kawagoe, 2026, Comprehensive synthesis of side-chain fluorinated 2α-[2-(Tetrazol-2-yl)ethyl]-1α,25-dihydroxyvitamin D3 analogs and preliminary biological activities [DOI]
24. 24 Arai, 2007, High-throughput system for analyzing ligand-induced cofactor recruitment by vitamin D receptor [DOI]
25. 25 Onate, 1995, Sequence and characterization of a coactivator for the steroid hormone receptor superfamily [DOI]
26. 26 Voegel, 1996, TIF2, a 160 kDa transcriptional mediator for the ligand-dependent activation function AF-2 of nuclear receptors [DOI]
27. 27 Feldman, 2018, Genome-wide perspectives on vitamin D receptor-mediated control of gene expression in target cells

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