title: Crystallographic and spectroscopic study on a known orally active progestin.
abstract: 6,17α-Dimethyl-4,6-pregnadiene-3,20-dione (medrogestone, 2) is for a long time known steroid endowed with progestational activity. In order to study its crystallographic and NMR spectroscopic properties with the aim to fill the literature gap, we prepared medrogestone following a traditional procedure. A careful NMR study allowed the complete assignment of the (1)H and (13)C NMR signals not only of medrogestone but also of its synthetic intermediates. The structural and stereochemical characterizations of medrogestone together with its precursor 17α-methyl-3-ethoxy-pregna-3,5-dien-20-one were described by means of X-ray analysis, allowing a deepened conformational investigation.
authors.affiliation: Dipartimento di Biotecnologie Mediche e Medicina Traslazionale, Università degli Studi di Milano, Via Saldini 50, 20133 Milano, Italy. Electronic address: patrizia.ferraboschi@unimi.it.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Ferraboschi
authors.affiliation: Dipartimento di Scienze Biomediche e Cliniche "Luigi Sacco", Università degli Studi di Milano, Via G.B. Grassi 74, 20157 Milano, Italy.
authors.forename: Pierangela
authors.initials: P
authors.lastname: Ciuffreda
authors.affiliation: Dipartimento di Biotecnologie Mediche e Medicina Traslazionale, Università degli Studi di Milano, Via Saldini 50, 20133 Milano, Italy.
authors.forename: Samuele
authors.initials: S
authors.lastname: Ciceri
authors.affiliation: EUTICALS SpA, Via Volturno 41/43, 20089 Rozzano, MI, Italy.
authors.forename: Paride
authors.initials: P
authors.lastname: Grisenti
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.
authors.forename: Carlo
authors.initials: C
authors.lastname: Castellano
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milano, Italy.
authors.forename: Fiorella
authors.initials: F
authors.lastname: Meneghetti
mesh_terms: D000284:Administration, Oral; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008524:Medrogestone / Q000008:administration & dosage / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D008524:Medrogestone
keywords: Medrogestone; NMR; Progesterone; Progestin; Steroidal hormone; X-ray