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Issue 0, 1973
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17,21-Dihydroxy-5β-pregn-2-ene-1,11,20-trione, a new analogue of cortisone. Methods for distinguishing between Δ2-1-oxo- and Δ1-3-oxo-steroids

Abstract

17,21-Dihydroxy-5β-pregn-2-ene-1,11,20-trione (9), a new analogue of cortisone, has been prepared from 1β,3α,17,20β,21-pentahydroxy-5β-pregnan-11-one, and compared with known analogues, namely ‘isocortisone’(11) and ‘Δ1-allocortisone’(2). The chief characteristic of the new analogue is its instability, which is attributed to interaction between the C-1 and C-11 carbonyl groups with resulting conformational distortion.

A study has been made of the u.v. and i.r. absorption and rotational characteristics of eleven matched pairs of Δ2-1-oxo-Δ1-oxo-steroids in order to better characterise and differentiate them. Significant and consistent differences were noted in their extinction coefficients, in the C[double bond, length as m-dash]C stretching bands of their i.r. spectra, and in their MD values. Examples of C-1 carbonyl : C-10 methyl and C-1 carbonyl : C-11 carbonyl group interactions, derived from MD considerations, also were encountered.

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Article type: Paper
DOI: 10.1039/P19730001361
Citation: J. Chem. Soc., Perkin Trans. 1, 1973,0, 1361-1365
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    17,21-Dihydroxy-5β-pregn-2-ene-1,11,20-trione, a new analogue of cortisone. Methods for distinguishing between Δ2-1-oxo- and Δ1-3-oxo-steroids

    J. J. Schneider, J. Chem. Soc., Perkin Trans. 1, 1973, 0, 1361
    DOI: 10.1039/P19730001361

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