PMID- 15110838
OWN - NLM
STAT- MEDLINE
DCOM- 20041210
LR  - 20061115
IS  - 0968-0896 (Print)
IS  - 0968-0896 (Linking)
VI  - 12
IP  - 10
DP  - 2004 May 15
TI  - ERbeta ligands. Part 2: Synthesis and structure-activity relationships of a 
      series of 4-hydroxy-biphenyl-carbaldehyde oxime derivatives.
PG  - 2553-70
AB  - A series of biphenyl carbaldehyde oximes (6) was prepared and shown to have 
      significant selectivity for the estrogen receptor-beta (ERbeta). The exploitation 
      of the oxime moiety as a hydrogen bond donating group, which mimicked the C-ring 
      of genistein makes these compounds unique. Molecular modeling studies showed the 
      oxime moiety hydrogen bonding to the histidine residue, which was supported by 
      the structure-activity relationships. The most potent compounds in this study had 
      IC50 values in a radioligand binding assay of between 8-35 nM. Among the most 
      selective compounds were 6i and 6s (49- and 31-fold ERbeta selective, 
      respectively).
FAU - Yang, Cuijian
AU  - Yang C
AD  - Chemical Sciences, Wyeth Research, 500 Arcola Road, Collegeville, PA 19426, USA.
FAU - Edsall, Richard Jr
AU  - Edsall R Jr
FAU - Harris, Heather A
AU  - Harris HA
FAU - Zhang, Xiaochun
AU  - Zhang X
FAU - Manas, Eric S
AU  - Manas ES
FAU - Mewshaw, Richard E
AU  - Mewshaw RE
LA  - eng
PT  - Journal Article
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (4-hydroxy-biphenyl-carbaldehyde oxime)
RN  - 0 (Biphenyl Compounds)
RN  - 0 (Estrogen Receptor alpha)
RN  - 0 (Estrogen Receptor beta)
RN  - 0 (Ligands)
RN  - 0 (Oximes)
RN  - 0 (RNA, Messenger)
RN  - 68238-35-7 (Keratins)
SB  - IM
MH  - Binding, Competitive
MH  - Biphenyl Compounds/chemical synthesis/chemistry/pharmacology
MH  - Cell Line, Tumor
MH  - Estrogen Receptor alpha/agonists/antagonists & inhibitors
MH  - Estrogen Receptor beta/*agonists/*antagonists & inhibitors
MH  - Gene Expression Regulation/genetics
MH  - Humans
MH  - Keratins/genetics
MH  - Ligands
MH  - Molecular Conformation
MH  - Molecular Structure
MH  - Oximes/*chemical synthesis/chemistry/*pharmacology
MH  - Quantitative Structure-Activity Relationship
MH  - RNA, Messenger/analysis
MH  - Radioligand Assay
EDAT- 2004/04/28 05:00
MHDA- 2004/12/16 09:00
CRDT- 2004/04/28 05:00
PHST- 2003/10/27 00:00 [received]
PHST- 2004/03/04 00:00 [revised]
PHST- 2004/03/14 00:00 [accepted]
PHST- 2004/04/28 05:00 [pubmed]
PHST- 2004/12/16 09:00 [medline]
PHST- 2004/04/28 05:00 [entrez]
AID - S0968089604002135 [pii]
AID - 10.1016/j.bmc.2004.03.028 [doi]
PST - ppublish
SO  - Bioorg Med Chem. 2004 May 15;12(10):2553-70. doi: 10.1016/j.bmc.2004.03.028.