Pyrazolo[1,5-a]pyrimidines as estrogen receptor ligands: defining the orientation of a novel heterocyclic core.
We have examined the pyrazolo[1,5-a]pyrimidine scaffold as a novel core structure for estrogen receptor ligands. Attachment of various substituents has helped to define the orientation of this heterocycle in the ligand-binding pocket as one in which a pendant phenol rather than the hydroxylpyrimidine serves as a mimic of the A-ring of estradiol.
Compton
Dennis R
DR
Department of Chemistry, University of Illinois, 600 S. Matthews Avenue, Urbana, IL 61801-3731, USA.
Carlson
Kathryn E
KE
Katzenellenbogen
John A
JA
D001665:Binding Sites; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D011743:Pyrimidines / Q000138:chemical synthesis / Q000494:pharmacology*; D011960:Receptors, Estrogen / Q000737:chemistry / Q000187:drug effects*; D013329:Structure-Activity Relationship
D006571:Heterocyclic Compounds; D008024:Ligands; D011720:Pyrazoles; D011743:Pyrimidines; D011960:Receptors, Estrogen