[Unexpected formation of an estrone derivative from androsta-1,4-diene-3,17-dione].
Reaction of androsta-1,4-diene-3,17-dione (1) with pyrrolidine and p-toluenesulfonic acid in toluene gives 3-pyrrolidino-estra-1,3,5(10)-triene-6,17-dione (7) in poor yield, whose structure is shown by X-ray analysis. Compared with 3H-estradiol, compound 7 shows only a weak receptor binding activity tested in an in vitro screening using rabbit uterus cytosol.
Görlitzer
K
K
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Bonnekessel
Ch
Ch
Jones
P G
PG
Kaufmann
G
G
D000730:Androstadienes / Q000737:chemistry* / Q000378:metabolism; D000818:Animals; D018360:Crystallography, X-Ray; D003600:Cytosol / Q000378:metabolism; D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D005260:Female; D066298:In Vitro Techniques; D008958:Models, Molecular; D008968:Molecular Conformation; D011817:Rabbits; D011960:Receptors, Estrogen / Q000187:drug effects / Q000378:metabolism; D014599:Uterus / Q000378:metabolism
C471748:3-pyrrolidino-estra-1,3,5(10)-triene-6,17-dione; D000730:Androstadienes; D011960:Receptors, Estrogen; C006573:1,4-androstadiene-3,17-dione; D004970:Estrone