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  • Title: [Relation of the progestagenic activity and conformation of the 17beta-acetyl side chain in the D'6-pentarane series].
    Author: Kamernitskiĭ AV, Levina IS, Kulikova LE, Korkhov VV, Nikitina GV.
    Journal: Bioorg Khim; 1988 Jun; 14(6):828-33. PubMed ID: 3190773.
    Abstract:
    The synthesis of 2' beta-methyl-16 alpha,17 alpha-cyclohexanoprogesterone and its MM2 conformational analysis have been performed. The acetyl side chain was shown to have an unusual conformation with the torsion angle C13-C17-C20-O20 being -32.1 degrees. This conformation is by 5.4 kJ.mol-1 more stable than the usual one with the torsion angle 130.3 degrees. 2' beta-Methyl-16 alpha,17 alpha-cyclohexanoprogesterone proved to be inactive as a progestogen (pregnancy maintenance and McPhail tests). The lack of the activity may be due to the additional methyl group in D'-ring causing a change of the conformation of the 17 beta-acetyl side chain, thus hindering the formation of the conformation necessary for binding to the progesterone receptor.
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