Colombo Diego, Ferraboschi Patrizia, Prestileo Paolo, Toma Lucio
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133 Milano, Italy.
J Steroid Biochem Mol Biol. 2006 Jan;98(1):56-62. doi: 10.1016/j.jsbmb.2005.07.009. Epub 2005 Oct 10.
6-Dehydroretroprogesterone (dydrogesterone) and three other natural or synthetic progestins (progesterone, retroprogesterone, and 6-dehydroprogesterone) were submitted to a conformational study through theoretical calculations at the B3LYP/6-31G(*) level and high field NMR spectroscopy. The study allows to define the role of the two structural features which differentiate these steroids, i.e., the C9 and C10 configuration and the C6-C7 unsaturation. The combined effects of the conformational preference of A ring, determined by the configuration at C9 and C10, and the enhanced rigidity due to the C6-C7 double bond, could account both for the higher activity and selectivity of dydrogesterone with respect to the other three steroids.
通过在B3LYP/6 - 31G(*)水平上的理论计算和高场核磁共振光谱，对6 - 脱氢逆孕酮（地屈孕酮）以及其他三种天然或合成孕激素（孕酮、逆孕酮和6 - 脱氢孕酮）进行了构象研究。该研究有助于确定区分这些甾体的两个结构特征的作用，即C9和C10构型以及C6 - C7不饱和键。由C9和C10构型决定的A环构象偏好以及C6 - C7双键导致的刚性增强的综合效应，既可以解释地屈孕酮相对于其他三种甾体具有更高的活性和选择性的原因。
