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New antiestrogens from a library screen of homoallylic amides, allylic amides, and C-cyclopropylalkylamides.

Abstract：

:A new structural scaffold for antiestrogens was identified from the cell-based screening of transcriptional regulation properties of a 67-member library of homoallylic amides, allylic amides, and C-cyclopropylalkylamides. C-Cyclopropylalkylamide 3a (O-ethyl-N-{2-[(1S*,2R*)-2-{(R*)-[(diphenylphosphinoyl)amino](phenyl)methyl}cyclopropyl]ethyl}-N-[(4-methylphenyl)sulfonyl]carbamate) had antagonistic activity similar to that of tamoxifen and was further evaluated. Compound 3a inhibited estradiol-induced proliferation of the ER-positive MCF-7 cells but had no effect on ER-negative MDA-MB231 human breast cancer cells. Furthermore, high micromolar concentrations of 3a exhibited minimal cytotoxicity to the ER-negative line. The biological activities of the enantiomers of 3a did not differ from one another nor from that of racemic 3a.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Janjic JM,Mu Y,Kendall C,Stephenson CR,Balachandran R,Raccor BS,Lu Y,Zhu G,Xie W,Wipf P,Day BW

doi

10.1016/j.bmc.2004.09.048

subject

Has Abstract

pub_date

2005-01-03 00:00:00

pages

157-64

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(04)00763-1

journal_volume

13

pub_type

杂志文章

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