title: Studies on modified estrogens: towards the synthesis of novel 14,15-cyclopropa[a]estra-1,3,5(10),8-tetraenes.
abstract: To improve the ratio of non-hormonal to hormonal activity, estrogens 3 and 4 were modified at various molecule positions. Isomerization of the 14 alpha,15 alpha-methylene bridge, controlled 3-methoxy group cleavage with respect to the 14 alpha,15 alpha-methylene bridge stereochemistry, reduction of the 8-double bond, and substitution of the oxyfunctionality at C-17 by a methylene and a difluoromethylene moiety were in the focus. As a result of in vivo and in vitro tests, compounds 27 and 29 were selected as potential follow-up candidates of lead 3.
authors.affiliation: Division of Research and Development, Jenapharm GmbH & Co. KG, Jena, Germany. Sigfrid.schwarz@web.de
authors.forename: S
authors.initials: S
authors.lastname: Schwarz
authors.forename: I
authors.initials: I
authors.lastname: Thieme
authors.forename: D
authors.initials: D
authors.lastname: Kosemund
authors.forename: B
authors.initials: B
authors.lastname: Undeutsch
authors.forename: M
authors.initials: M
authors.lastname: Kummer
authors.forename: H
authors.initials: H
authors.lastname: Görls
authors.forename: W
authors.initials: W
authors.lastname: Römer
authors.forename: G
authors.initials: G
authors.lastname: Kaufmann
authors.forename: W
authors.initials: W
authors.lastname: Elger
authors.forename: A
authors.initials: A
authors.lastname: Hillisch
authors.forename: B
authors.initials: B
authors.lastname: Schneider
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D045166:Estradiol Congeners / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
chemical_list: D000975:Antioxidants; D003521:Cyclopropanes; D045166:Estradiol Congeners; D007202:Indicators and Reagents; D004958:Estradiol