Structural requirements for progestational activity. Synthesis and properties of rac-8alpha,9beta,10alpha,14beta-progesterone.
rac-8alpha,9beta,10alpha,14beta-Progesterone, 1, has been synthesized and subjected to X-ray crystallographic analysis which established that the ring conformations are A, 1beta-sofa; B, chair; C, chair; and D, intermediate between an envelope and a half-chair. This compound is 10% as active as progesterone in the Clauberg assay and has an affinity for the uterine cytosol (rabbit) receptor for progesterone 2% as great as that of progesterone.
D000818:Animals; D005260:Female; D008958:Models, Molecular; D008968:Molecular Conformation; D011374:Progesterone / Q000138:chemical synthesis* / Q000494:pharmacology; D011372:Progestins; D011817:Rabbits; D011980:Receptors, Progesterone / Q000187:drug effects; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects; D014961:X-Ray Diffraction
D011372:Progestins; D011980:Receptors, Progesterone; D011374:Progesterone