caa a22 4500 465806023 CHVBK 20180323112104.0 cr unu---uuuuu 170327e19901201xx s 000 0 eng 10.1007/BF03349652 doi (NATIONALLICENCE)springer-10.1007/BF03349652 Structure-activity and structure-affinity relationships of 19-nor-progesterone derivatives in rat uterus [Elektronische Daten] [J. Botella, I. Duc, R. Delansorne, J. Paris, B. Lahlou] 19-nor-progesterone (19NP) is a potent progestagen which possesses a high affinity for the progesterone receptor (PgR). In contrast, 17α-hydroxylated-progesterone (170HP) shows no hormonal activity and does not compete with progesterone (P) for the PgR. The aim of the present work was to analyse in parallel the structureaffinity and the structure-activity relationships for new molecules obtained by modifications of 19NP and 170HP. The attachment of a 17α-hydroxyl group on 19NP led to a dramatic decrease in both affinity and activity for the end-product, 17α-hydroxylated-19-nor-progesterone (17OH-19NP). The further addition of a methyl group combined with the formation of a double-bound at C6 on 17OH-19NP results in nomegestrol (NOM), the relative affinity of which remained low. Negligible activity was also associated with this affinity in comparison to the parent 19NP. Strikingly, the protection of the free 17α-hydroxyl group of NOM by an acetate led to a potent progestin with high affinity for PgR. It is concluded that the sum of the modifications brought into the 17OHP-19NP molecule reestablishes both affinity and activity of the original 19NP molecule. The same conclusion holds if P is considered as the parent compound, as already stated in the literature. Italian Society of Endocrinology (SIE), 1990 Receptors nationallicence uterus nationallicence rat nationallicence progestin nationallicence nomegestrol acetate nationallicence Botella J. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut Duc I. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut Delansorne R. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut Paris J. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut Lahlou B. Laboratoire de Physiologie Cellulaire et Comparée, Université de Nice Sophia Antipolis, Nice, France aut Journal of Endocrinological Investigation Springer International Publishing 13/11(1990-12-01), 905-910 0391-4097 13:11<905 1990 13 40618 https://doi.org/10.1007/BF03349652 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF03349652 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Botella J. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut NATIONALLICENCE 700 1- Duc I. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut NATIONALLICENCE 700 1- Delansorne R. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut NATIONALLICENCE 700 1- Paris J. Service de Biologie Cellulaire. Laboratoire Theramex, 4-6 av. Prince Héréditaire Albert, 98000, Principauté de Monaco, France aut NATIONALLICENCE 700 1- Lahlou B. Laboratoire de Physiologie Cellulaire et Comparée, Université de Nice Sophia Antipolis, Nice, France aut NATIONALLICENCE 773 0- Journal of Endocrinological Investigation Springer International Publishing 13/11(1990-12-01), 905-910 0391-4097 13:11<905 1990 13 40618 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer