Design and synthesis of 1 α,25-dihydroxyvitamin D3 analogues with fixed torsion angle C(16-17-20-22)

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4725-4728

  Martínez Pérez, JoséAntonio ^a,d   Sarandeses, Luis ^b   Granja, Juan ^a   Palenzuela, José Antonio ^c   Mouriño, Antonio ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

^d UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Hormone 1 ,25 dihydroxyvitamin D3; Molecular mechanics; Vitamin D receptor (VDR)

Indexed keywords

CALCITRIOL DERIVATIVE; VITAMIN D RECEPTOR;

ARTICLE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MECHANICS; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STEREOCHEMISTRY;

EID: 0032566030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00867-3     Document Type: Article

References (20)

1. [1] Feldman D, Glorieux FH, Pike JW, editors. Vitamin D. San Diego: Academic Press, 1997.
2. [2] Norman AW, Bouillon R, Thomasset M, editors. Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone. Riverside-CA: Vitamin D Workshop Inc., 1997.
3. [3] Bouillon R, Okamura WH, Norman AW. Structure-function Relationships in the Vitamin D Endocrine System. Endocr. Rev. 1995;16:200-257.
4. [4] Valaja T, Mahonen A, Pirskanen A, Mäenpää PH. Biochem. Biophys. Res. Commun. 1990;169:629-635.
5. [5] Peleg S, Sastry M, Collins ED, Bishop JE, Norman AW. J. Biol. Chem. 1995;270:10551-10558.
6. [6] Yamamoto K, Sun WY, Ohta M, Hamada K, DeLuca HF, Yamada S. J. Med. Chem. 1996;39:2727-2737, and references therein.
7. [7] Yamamoto K, Ohta M, DeLuca HF, Yamada S. Bioorg. Med. Chem. Lett. 1995;5:979-984.
8. [8] Yamamoto K, Takahashi J, Hamano K, Yamada S, Yamaguchi K, DeLuca HF. J. Org. Chem. 1993;58:2530-2537.
9. [9] MMX (an enhanced version of MM2) was calculated by using software PCMODEL (Serena Software, Bloomington).
10. [10] Okamura WH, Palenzuela JA, Plumet J, Midland MM. J. Cell. Biochem. 1992;49:10-18.
11. [11] Zhu G-D, Okamura WH. Synthesis of vitamin D (calciferol). Chem. Rev. 1995;95:1877-1952.
12. [12] Dai H, Posner GH. Synthetic approaches to vitamin D. Synthesis 1994;1383-1398.
13. [13] Fernández B, Martínez-Pérez JA, Granja JR, Castedo L, Mouriño A. J. Org. Chem. 1992;57:3173-3178.
14. [14] Maryanoff BE, Reitz AB, Duhl-Emswiler BA. J. Am. Chem. Soc. 1985;107:217-226.
15. [15] Vedejs E, Fuchs PL. J. Am. Chem. Soc. 1973;95:822-825.
16. [16] Mascareñas JL, Sarandeses LA, Castedo L, Mouriño A. Tetrahedron 1991;47:3485-3498.
17. [17] Juliá S, Ginebreda A. Synthesis 1977;682-683.
18. [18] Walborsky HM, Ollman J, Hamdouchi C, Topolski M. Tetrahedron Lett. 1992;33,761-764.
19. [19] Lythgoe B. Chem. Soc. Rev. 1980;9:449-475.
20. [20] Baggiolini EG, Iacobelli JA, Hennessy BM, Batcho AD, Sereno JF, Uskokovic MR. J. Org. Chem. 1986;51:3098-3108.