Back to Search Start Over

Synthesis, biological activity, and conformational analysis of CD-ring modified trans-decalin 1 alpha,25-dihydroxyvitamin D analogs.

Authors :
Chen YJ
Gao LJ
Murad I
Verstuyf A
Verlinden L
Verboven C
Bouillon R
Viterbo D
Milanesio M
Van Haver D
Vandewalle M
De Clercq PJ
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2003 Jan 21; Vol. 1 (2), pp. 257-67.
Publication Year :
2003

Abstract

A novel series of analogs of 1,25-dihydroxyvitamin D3, the hormonally active metabolite of vitamin D3, characterised by the presence of a trans-fused decalin CD-ring system, possesses surprising biological activities in combination with specific structural modifications in the flexible parts of the molecule, when compared with the natural hydrindane derivatives. (1) A large difference in biological activity is observed between the 20-epimeric trans-decalin analogs that follows a pattern opposite to what is usually observed for the natural ring size. (2) Several trans-decalin analogs that are modified in the seco-B-ring region, including previtamin derivatives, possess a pronounced vitamin D-like activity, whereas the corresponding hydrindane derivatives are inactive. The molecular origin of this behavior is still under study.

Details

Language :
English
ISSN :
1477-0520
Volume :
1
Issue :
2
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
12929421
Full Text :
https://doi.org/10.1039/b209147j