TY - JOUR
T1 - Diaryl-dialkyl-substituted pyrazoles
T2 - Regioselective synthesis and binding affinity for the estrogen receptor
AU - Nishiguchi, Gisele A.
AU - Rodriguez, Alice L.
AU - Katzenellenbogen, John A.
N1 - Funding Information:
This work was supported by a grant from the National Institutes of Health (PHS 5R37 DK15556). We are grateful to Kathryn Carlson for biological assays and Dorina Kosztin for assistance with molecular modeling studies.
PY - 2002/3/25
Y1 - 2002/3/25
N2 - We have developed two novel series of tetrasubstituted pyrazoles, embodying 1,3-diaryl-4,5-dialkyl or 3,5-diaryl-1,4-dialkyl substitution patterns. The scope of a regioselective method, developed by us earlier, was expanded to allow the synthesis of the first series of these tetrasubstituted pyrazoles directly from α,β-unsaturated ketones. The binding affinity of some of these pyrazoles for the estrogen receptor (ER) subtypes ERα and ERβ is very high, and the overall affinity pattern suggests the importance of three phenol substituents for high affinity, ERα-selective binding.
AB - We have developed two novel series of tetrasubstituted pyrazoles, embodying 1,3-diaryl-4,5-dialkyl or 3,5-diaryl-1,4-dialkyl substitution patterns. The scope of a regioselective method, developed by us earlier, was expanded to allow the synthesis of the first series of these tetrasubstituted pyrazoles directly from α,β-unsaturated ketones. The binding affinity of some of these pyrazoles for the estrogen receptor (ER) subtypes ERα and ERβ is very high, and the overall affinity pattern suggests the importance of three phenol substituents for high affinity, ERα-selective binding.
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U2 - 10.1016/S0960-894X(02)00057-4
DO - 10.1016/S0960-894X(02)00057-4
M3 - Article
C2 - 11959000
AN - SCOPUS:0037170775
SN - 0960-894X
VL - 12
SP - 947
EP - 950
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 6
ER -