Convergent synthesis, chiral HPLC, and vitamin D receptor affinity of analogs of 1,25-dihydroxycholecalciferol

Chirality

Volumn 11, Issue 3, 1999, Pages 249-255

  Odrzywolska, Małgorzata ^a   Chodynski, Michał ^a   Halkes, Sebastian J ^b   Van De Velde, Jan Paul ^b   Fitak, Hanna ^a   Kutner, Andrzej ^a  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b Solvay Pharmaceuticals Inc   (Netherlands)

Author keywords

(+) (R) 2 methylglycidol; ( ) (S) 2 methylglycidol; Chiral stationary phase HPLC; Convergent synthesis; Vitamin D synthons

Indexed keywords

CALCITRIOL DERIVATIVE; VITAMIN D RECEPTOR;

ARTICLE; CHIRALITY; DRUG DETERMINATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PRIORITY JOURNAL; RECEPTOR AFFINITY;

EID: 0033046786     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:3<249::AID-CHIR12>3.0.CO;2-V     Document Type: Article

References (36)

1. Ettinger RA, DeLuca HF. The vitamin D endocrine system and its therapeutic potential. Adv Drug Res 1996;28:269-312.
2. DeLuca HFD. Historical overview. In: Feldman D, Glorieux FH, Pike JW, editors. Vitamin D. San Diego: Academic Press; 1997. p 3-11.
3. Bouillon R, Okamura WH, Norman AW. Structure-function relationships in the vitamin D endocrine system. Endocrine Rev 1995;16:200-257.
4. Zhu G-D, Okamura WH. Synthesis of vitamin D (Calciferol). Chem Rev 1995;95:1877-1952.
5. Midland MM, Hammond MW, Rahman NA, Dormanen MC, Nemere I, Norman AW. Chemistry and conformation of vitamin D molecules. J Steroid Biochem Mol Biol 1995;53:603-613.
6. Dai H, Posner GH. Synthetic approaches to vitamin D. Synthesis 1994;1383-1398.
7. Wilson SR, Yasmin A. Stereoselective synthesis of vitamin D. In: Attaur-Rahman, editor. Studies in natural products chemistry. Vol. 10. Amsterdam: Elsevier Science Publishers; 1992. p 43-75.
8. Okamura WH, Zhu G-D. Chemistry and design: structural biology of vitamin D action. In: Feldman D, Glorieux FH, Pike JW, editors. Vitamin D. San Diego: Academic Press; 1997:939-971.
9. 3 function as ligands for the D-binding protein, nuclear receptor and membrane receptor: a status report. J Steroid Biochem Mol Biol 1996;56:13-22.
10. Bouillon R, Verstuyf A, Verlinden A, Allewart K, Branisteanu D, Mathieu C, van Baelen H. Non-hypercalcemic pharmacological aspects of vitamin D analogs. Biochem Pharmacol 1995;50:577-583.
11. Darwish H, DeLuca HF. Vitamin D-regulated gene expression. Crit Rev Eukar Gene Expr 1993;3:89-116.
12. DeLuca HF. Applications of new vitamin D compounds to disease. Drug News Perspec 1992;5:87-92.
13. Rastinejad F, Perlmann T, Evans RM, Sigler PB. Structural determinants of nuclear receptor assembly on DNA direct repeats. Nature 1994;375:203-211.
14. 3: synthesis, isomerization to previtamins, and biological studies. J Med Chem 1994; 37:2387-2393.
15. 3 hybrid analogs with structural changes at both the A-ring and the C,D-ring side chain. II. Bioorg Med Chem Lett 1995;5:2163-2168.
16. 3 receptor. J Org Chem 1985;13:158-169.
17. 3. J Org Chem 1995;60:1828-1833.
18. 3. J Org Chem 1993;58:1895-1899.
19. Chodyński M, Kutner A. Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol. Steroids 1991;56:311-315.
20. Hollis BW. Assay of a circulating 1,25-dihydroxyvitamin D involving a novel single cartridge extraction and purification procedure. Clin Chem 1986;32:2060-2063.
21. 2 (calciferol). J Org Chem 1986;51:4819-4828.
22. 3 analogs with modified side chains. Tetrahedron Lett 1994;35:275-278.
23. 3, a useful vitamin D metabolism probe. Tetrahedron 1993;49:739-746.
24. Kutner A, Perlman LK, Siciński RR, Phelps ME, Schnoes HK, DeLuca HF. Vitamin D C-22 aldehyde. New key intermediate for the synthesis of side-chain modified vitamin D analogs. Tetrahedron Lett 1987;28: 6129-6132.
25. Kutner A, Perlman KL, Lago A, Siciński RR, Schnoes HK, DeLuca HF. Novel convergent sythesis of side-chain modified analogs of 1α,25-dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol. J Org Chem 1988;53:3450-3457.
26. 3: 24,24-dihomo-25-hydroxycholecalciferol and (22E)-22-dehydro-24,24-dihomo-25-dihydroxycholecalciferol. Bioorg Chem 1993;21:13-23.
27. Chodyński M, Wjoceichowska W, Halkes SJ, van de Velde J-P, Kutner A. Synthesis and in vitro evaluation of side-chain unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol. Steroids 1997;62: 546-553.
28. Shao H, Zhu Q, Goodman M. A new asymmetric synthesis of α-methylcysteines via chiral aziridines. J Org Chem 1995;60:790-791.
29. Scherkenbeck J, Bart M, Thiel U, Metten K-H, Heinemann F, Welzel P. Model studies directed toward forskolin: synthesis of a tricyclic model compound from farnesol. Tetrahedron 1988;44:6325-6336.
30. 3. Tetrahedron Lett 1993; 34:6533-6536.
31. Odrzywolska M, Chodyński M, Halkes SJ, van de Velde J-P, Kutner A. Pol. Patent P-316696, 1996.
32. Yashima E, Kasashima E, Okamoto Y. Enantioseparation on 4-halogen-substituted phenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography. Chirality 1997;9:63-68, and references cited therein.
33. Dingenen J. Polysaccharide phases in enantioseparations. In: Subramanian G, editor. A practical approach to chiral separations by liquid chromatography. New York: VCH Publishers; 1994. p 115-181.
34. 3. J Bone Min Metab 1991;9:171-179.
35. Kutner A. Novel practical synthesis of 24,24-dihomo-1,25-dihydroxycholecalciferol. Pol J Chem 1993;67:759-761.
36. 3 compounds: separation of calcium and cell differentiation activities. Biochemistry 1990;29:190-196.