Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemical Modifications of Androsta-1, 4-diene-3, 17-dione. II. Synthesis of 17-nor-Vitamin D Analogues having a Hydroxy Group at 1α- or 2β-Position and Biological Activity of 1α-Hydroxy-17-nor-17, 17-ethylenedioxyvitamin D
HARUO SAKAMOTOAKIKO SUGIMOTOCHIKARA KANEKOTATSUO SUDASATOSHI SASAKI
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1975 Volume 23 Issue 8 Pages 1733-1737

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Abstract
Using 1α- and 2β-hydroxy derivatives of 3β-hydroxy-17, 17-ethylenedioxyandrosta-5, 7-diene obtained in our previous work as starting materials, 1α- and 2β-hydroxylated analogues of 17-nor-17, 17-ethylenedioxyvitamin D have been prepared via (i) photochemical conrotatory opening of the B-ring and (ii) the subsequent thermal 1, 7-antarafacial hydrogen shifts. 1α-Hydroxy-17, 17-ethylenedioxyvitamin D showed no significant antirachitic activity in rats. This fact seems to suggest that, in addition to the 1α-hydroxy function, the presence of the side chain in the vitamin D system plays also an important role in the biological action of the D analogues.
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© The Pharmaceutical Society of Japan
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