title: 1,3-Diaxially substituted trans-decalins: potential nonsteroidal human progesterone receptor inhibitors.
abstract: On the basis of molecular modeling and QSAR analysis of the known human progesterone receptor (hPR) inhibitor Mifepristone (RU-486) and other hPR ligands, a new class of potential nonsteroidal hPR inhibitors was designed. The parent racemic compound 1 was synthesized through an efficient 13-step synthetic pathway. The key constructive steps are a stereoselective epoxide ring opening and the reductive Heck cyclization to form the main framework of (+/-)-1. The current established flexible synthetic route allows for further chemical diversification.
authors.affiliation: Department of Medicinal Chemistry, The University of Mississippi, P.O. Box 1848, University, Mississippi 38677, USA.
authors.forename: Ze
authors.initials: Z
authors.lastname: Li
authors.forename: E Blake
authors.initials: EB
authors.lastname: Watkins
authors.forename: Hua
authors.initials: H
authors.lastname: Liu
authors.forename: Amar G
authors.initials: AG
authors.lastname: Chittiboyina
authors.forename: Paulo B
authors.initials: PB
authors.lastname: Carvalho
authors.forename: Mitchell A
authors.initials: MA
authors.lastname: Avery
mesh_terms: D003500:Cyclization; D004852:Epoxy Compounds; D006801:Humans; D008024:Ligands; D015735:Mifepristone; D008958:Models, Molecular; D009281:Naphthalenes / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D011980:Receptors, Progesterone / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D008024:Ligands; D009281:Naphthalenes; D011980:Receptors, Progesterone; D015735:Mifepristone; C007229:decalin