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.
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.
Lazar
Dusan
D
Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 4, 21000 Novi Sad, Yugoslavia. dlazar@im.ns.ac.yu
Stanković
Slobodanka
S
Pejanović
Vjera
V
Courseille
Christiane
C
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
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