title: Stereoselective synthesis of F-ring saturated estrone-derived inhibitors of Hedgehog signaling based on cyclopamine.
abstract: Previous work in this laboratory established that the readily available F-ring aromatic analog of cyclopamine is a highly potent inhibitor of Hedgehog signaling. The synthesis and biological evaluation of two F-ring saturated analogs that are more potent than the F-ring aromatic structure are reported.
authors.affiliation: Department of Chemistry, The University of Pennsylvania , Philadelphia, Pennsylvania 19104, USA.
authors.forename: Zhihui
authors.initials: Z
authors.lastname: Zhang
authors.forename: Valérie
authors.initials: V
authors.lastname: Baubet
authors.forename: Christian
authors.initials: C
authors.lastname: Ventocilla
authors.forename: Chaomei
authors.initials: C
authors.lastname: Xiang
authors.forename: Nadia
authors.initials: N
authors.lastname: Dahmane
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Winkler
mesh_terms: D000818:Animals; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D003500:Cyclization; D004970:Estrone / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology*; D053823:Hedgehog Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D015398:Signal Transduction / Q000187:drug effects*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014704:Veratrum Alkaloids / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D053823:Hedgehog Proteins; D014704:Veratrum Alkaloids; D004970:Estrone; C000541:cyclopamine