Methyl-introduced A-ring analogues of 1α,25-dihydroxyvitamin D 3: Synthesis and biological evaluation

Anticancer Research

Volumn 26, Issue 4 A, 2006, Pages 2633-2636

  Fujishima, Toshie ^a,b   Tsutsumi, Ryuji ^b   Negishi, Yoichi ^c   Fujii, Shinya ^a   Takayama, Hiroaki ^b   Kittaka, Atsushi ^b   Kurihara, Masaaki ^d  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

^c TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^d NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

Author keywords

Chemical synthesis; Hormones; Receptors; Vitamins

Indexed keywords

2 METHYL 1,25 DIHYDROXYVITAMIN D3; 2,2 DIMETHYL 1,25 DIHYDROXYVITAMIN D3; CALCITRIOL DERIVATIVE; CARBON; METHYL GROUP; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; CELL DIFFERENTIATION; CONTROLLED STUDY; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ANIMALS; BONE NEOPLASMS; CALCITRIOL; CELL DIFFERENTIATION; HL-60 CELLS; HUMANS; OSTEOSARCOMA; RATS; RECEPTORS, CALCITRIOL;

EID: 33746643489     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (18)

1. Feldman D, Pike JW and Glorieux FH (eds.). Vitamin D. Burlington, Elsevier Academic Press, 2005.
2. 3. J Biol Chem 268: 20022-20030, 1993.
3. Bischof MG, Siu-Caldera ML, Weiskop Af, Vouros P, Cross HS, Peterlik M and Reddy GS: Differentiation related pathways of 1α,25- dihydroxycholecalciferol metabolism in human colon adenocarcinoma-derived Caco-2 cells. Production of 1α,25-dihydroxy-3-epi-cholecalciferol. Exp Cell Res 241: 194-201, 1998.
4. 3. Bioorg Med Chem Lett 8: 151-156, 1998.
5. 3 and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20. J Med Chem 43: 4247-4265, 2000.
6. 3 and their 20-epimers: possible binding modes of potent A-ring analogues to vitamin D receptor. Chem Biol 8: 1011-1024, 2001.
7. 3 and its 20-epimer. Biochem Pharmacol 59: 1937-1947, 2000.
8. 3: remarkably high affinity to vitamin D receptor. Org Lett 2: 2619-2622, 2000.
9. 3 analogues. Bioorg Med Chem Lett 10: 1129-1132, 2000.
10. 3 analogues and their docking to vitamin D receptor. J Org Chem 66: 8760-8711, 2001.
11. 3 assessed by NB4 cell differentiation. J Steroid Biochem Mol Biol 94: 469-479, 2005.
12. Rochel N, Wurtz JM, Mitschler A, Klaholz B and Moras D: The crystal structure of the nuclear receptor for vitamin D bound to its natural ligand. Mol Cell 5: 173-179, 2000.
13. Trost BM, Dumas J and Villa M: New strategies for the synthesis of vitamin D metabolites via Pd-catalyzed reactions. J Am Chem Soc 114: 9836-9845, 1992.
14. 3: A-ring structural motif that modulates interactions of vitamin D receptor with transcriptional coactivators. Org Biomol Chem 1: 1863-1869, 2003.
15. Konno K, Fujishima T, Liu ZP and Takayama H: Determination of absolute configuration of 1,3-diols by the modified Mosher's methods using their di-MTPA esters. Chirality 14: 72-80, 2002.
16. 3, the potent inducers of cell differentiation. J Steroid Mol Biol 89-90: 89-92, 2004.
17. Negishi Y, Kajiyama N, Kawashima K, Fujishima T, Takayama H, Endo H and Kawashima R: Establishment of permanent cell lines exhibiting vitamin D-dependent expression of β-galactosidase activity. Biochem Pharmacol 58: 465-470, 1999.
18. 3 potently stimulates gene-specific DNA binding of the vitamin D receptor in osteoblast. J Biol Chem 278: 31756-31765, 2003.