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Synthesis, biological activity, and conformational analysis of CD-ring modified trans-decalin 1
Yong-Jun Chen1, Ling-Jie Gao, Ibrahim Murad
1Laboratory for Organic Synthesis, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S4), B-9000 Gent, Belgium.
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.