title: D-Secoestrone derivatives. V1. 3-Methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile and 17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile.
abstract: The two title 16,17-secoestrone derivatives, 3-methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C(25)H(27)NO(2), (I) (17-oxo substituent), and 17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile, C(25)H(29)NO(2), (II) (17-hydroxy substituent), have quite different conformations in the solid state. These conformational differences can be minimized by molecular mechanics calculations. Thus, the remarkable difference in the biological activity of the two compounds, e.g. the strong oestrogenic characteristics of (I) and the moderate antioestrogenic action of (II), must be caused by the difference in substitution at C17. In (II), the molecules are linked by O-H...N hydrogen bonds, forming spirals along the b direction.
authors.affiliation: Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000 Novi Sad, Yugoslavia. dlazar@im.ns.ac.yu
authors.forename: Dusan
authors.initials: D
authors.lastname: Lazar
authors.forename: Slobodanka
authors.initials: S
authors.lastname: Stanković
authors.forename: Vjera
authors.initials: V
authors.lastname: Pejanović
authors.forename: Christiane
authors.initials: C
authors.lastname: Courseille
mesh_terms: D018360:Crystallography, X-Ray; D004965:Estrogen Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D012632:Secosteroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C454603:17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile; C454602:3-methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-nitrile; D004965:Estrogen Antagonists; D009570:Nitriles; D012632:Secosteroids