Synthesis and biological evaluation of novel 6-substituted analogs of 1α,25-dihydroxy-19-norvitamin D3

Journal of Steroid Biochemistry and Molecular Biology

Volumn 136, Issue 1, 2013, Pages 30-33

  Sokolowska, Katarzyna ^a,b,c   Sicinski, Rafal R ^a,b   Mouriño, Antonio ^c   Plum, Lori A ^a   DeLuca, Hector F ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WARSAW   (Poland)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

B seco steroids; Cellular HL 60 differentiation; VDR binding; Vitamin D analogs

Indexed keywords

1ALPHA,25 DIHYDROXY 19 NORVITAMIN D3; HYDROXYL GROUP; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D;

BIOLOGICAL ACTIVITY; CELL DIFFERENTIATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; IN VITRO STUDY; NONHUMAN; OLEFINATION; REVIEW; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

RATTUS;

EID: 84881191086     PISSN: 09600760     EISSN: 18791220     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2012.10.016     Document Type: Review

References (15)

1. H.F. DeLuca, H.K. Schnoes, Vitamin D: recent advances, Annual Review of Biochemistry 52 (1983)411-439. (Pubitemid 13030688)
2. E. Abe, C. Miyaura, T. Kuribayashi, K. Konno, Y. Nishii, T. Suda, 1a, 25-Dihydroxycholecalciferol and a human myeloid leukaemia cell line (HL-60), Biochemical Journal 204 (1982) 713-719.
3. T. Suda, T. Shinki, N. Takahashi, The role of vitamin D in bone and intestinal cell differentiation, Annual Review of Nutrition 10 (1990) 195-211.
4. R. Bouillon, W.H. Okamura, A. Norman, Structure-function relationship in the vitamin D endocrine system, Endocrine Reviews 16 (1995) 200-257.
5. G. Chiellini, H.F. DeLuca, The importance of stereochemistry on the actions of vitamin D, Current Topics in Medicinal Chemistry 11 (2011) 840-859.
6. K. Sokolowska, A. Mourino, R.R. Sicinski, R. Sigueiro, L.A. Plum, H.F. DeLuca, Synthesis and biological evaluation of 6-methyl analog of 1a, 25-dihydroxyvitamin D3, Journal of Steroid Biochemistry and Molecular Biology 121 (2010) 29-33.
7. K. Takenouchi, S. Ishizuka, T. Miura, A. Sato, T. Akimori, 6, 7-Substituted 19-norvitamin D3 derivatives and pharmaceuticals containing them, JP 2004-175763 A.
8. M.C. Dame, E.A. Pierce, J.M. Prahl, C.E. Hayes, H.F. DeLuca, Monoclonal antibodies to the porcine intestinal receptor for 1, 25-dihydroxyvitaminD3: interaction with distinct receptor domains, Biochemistry 25 (1986) 4523-4534. (Pubitemid 16010187)
9. V.C. Ostrem, W.F. Lau, S.H. Lee, K. Perlman, J. Prahl, H.K. Schnoes, H.F. DeLuca, N. Ikekawa, Induction of monocytic differentiation of HL-60 cells by 1, 25-dihydroxyvitamin D analogs, Journal of Biological Chemistry 262 (1987) 14164-14171. (Pubitemid 17152097)
10. N.C. Arbour, T.K. Ross, C. Zierold, J.M. Prahl, H.F. DeLuca, A highly sensitive method for large-scale measurements of 1, 25-dihydroxyvitamin D, Analytical Biochemistry 255 (1998) 148-154. (Pubitemid 28047631)
11. N. Miyaura, A. Suzuki, A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides, Tetrahedron Letters 20(1979)3437-3440.
12. N. Miyaura, A. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds, Chemical Reviews 95 (1995) 2457-2483.
13. T. Ishiyama, M. Murata, N. Miyaura, Synthesis of arylboronates via the palladium(0)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates, Journal of Organic Chemistry 60 (1995) 7508-7510.
14. K.L. Perlman, R.E. Swenson, H.E. Paaren, H.K. Schnoes, H.F. DeLuca, Novel synthesis of 19-norvitamin D compounds, Tetrahedron Letters 32 (1991) 7663-7666.
15. P. Gogoi, R. Sigueiro, S. Eduardo, A. Mourino, An expeditious route to 1a, 25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed A-ring closure and Suzuki coupling to the C/D unit, Chemistry-A European Journal 16 (2010) 1432-1435.