Practical Synthesis and Evaluation of the Biological Activities of 1α,25-dihydroxyvitamin D3 Antagonists, 1α,25-dihydroxyvitamin D3-26,23-lactams. Designed on the …
Y Nakano, Y Kato, K Imai, E Ochiai… - Journal of medicinal …, 2006 - ACS Publications
Y Nakano, Y Kato, K Imai, E Ochiai, J Namekawa, S Ishizuka, K Takenouchi, A Tanatani…
Journal of medicinal chemistry, 2006•ACS PublicationsA practical synthetic route to novel vitamin D antagonists of DLAM (1α, 25-dihydroxyvitamin
D3-26, 23-lactam) was developed from vitamin D2 via the 1, 3-dipolar cycloaddition reaction
as a key step. Six DLAM derivatives (24 compounds) with a variety of nitrogen substituents
and stereochemistries at C23 and C25 were synthesized. Among these new derivatives,(23
S, 25 S)-DLAM isomers bound effectively to VDRs and showed antagonistic activity in the
HL-60 cell differentiation inhibition assay. The importance of the substituent on the nitrogen …
D3-26, 23-lactam) was developed from vitamin D2 via the 1, 3-dipolar cycloaddition reaction
as a key step. Six DLAM derivatives (24 compounds) with a variety of nitrogen substituents
and stereochemistries at C23 and C25 were synthesized. Among these new derivatives,(23
S, 25 S)-DLAM isomers bound effectively to VDRs and showed antagonistic activity in the
HL-60 cell differentiation inhibition assay. The importance of the substituent on the nitrogen …
A practical synthetic route to novel vitamin D antagonists of DLAM (1α,25-dihydroxyvitamin D3-26,23-lactam) was developed from vitamin D2 via the 1,3-dipolar cycloaddition reaction as a key step. Six DLAM derivatives (24 compounds) with a variety of nitrogen substituents and stereochemistries at C23 and C25 were synthesized. Among these new derivatives, (23S,25S)-DLAM isomers bound effectively to VDRs and showed antagonistic activity in the HL-60 cell differentiation inhibition assay. The importance of the substituent on the nitrogen of DLAMs for antagonistic activity was also suggested by computational docking studies.
ACS Publications