eprintid: 20392
rev_number: 18
userid: 1419
dir: disk0/00/02/03/92
datestamp: 2014-01-30 17:03:43
lastmod: 2019-02-02 15:56:51
status_changed: 2014-01-30 17:03:43
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Janjic, JM
creators_name: Mu, Y
creators_name: Kendall, C
creators_name: Stephenson, CRJ
creators_name: Balachandran, R
creators_name: Raccor, BS
creators_name: Lu, Y
creators_name: Zhu, G
creators_name: Xie, W
creators_name: Wipf, P
creators_name: Day, BW
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creators_email: pwipf@pitt.edu
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title: New antiestrogens from a library screen of homoallylic amides, allylic amides, and C-cyclopropylalkylamides
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: A new structural scaffold for antiestrogens was identified from the cell-based screening of a 67-member library of homoallylic amides, allylic amides, and C-cyclopropylalkylamides. Several derivatives had activity comparable to that of tamoxifen. 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. © 2004 Elsevier Ltd. All rights reserved.
date: 2005-01-03
date_type: published
publication: Bioorganic and Medicinal Chemistry
volume: 13
number: 1
pagerange: 157 - 164
refereed: TRUE
issn: 0968-0896
id_number: 10.1016/j.bmc.2004.09.048
pmid: 15582460
mesh_headings: Amides--chemistry
mesh_headings: Amides--pharmacology
mesh_headings: Cell Line
mesh_headings: Cell Line, Tumor
mesh_headings: Drug Screening Assays, Antitumor
mesh_headings: Estrogen Receptor Modulators--chemistry
mesh_headings: Estrogen Receptor Modulators--pharmacology
mesh_headings: Genes, Reporter
mesh_headings: Humans
mesh_headings: Receptors, Estrogen--metabolism
mesh_headings: Structure-Activity Relationship
chemical_names: Amides
chemical_names: Estrogen Receptor Modulators
chemical_names: Receptors, Estrogen
citation:   Janjic, JM and Mu, Y and Kendall, C and Stephenson, CRJ and Balachandran, R and Raccor, BS and Lu, Y and Zhu, G and Xie, W and Wipf, P and Day, BW  (2005) New antiestrogens from a library screen of homoallylic amides, allylic amides, and C-cyclopropylalkylamides.  Bioorganic and Medicinal Chemistry, 13 (1).  157 - 164.  ISSN 0968-0896     
document_url: http://d-scholarship-dev.library.pitt.edu/20392/1/licence.txt