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
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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.
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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Janjic, JM | | | | Mu, Y | | | | Kendall, C | | | | Stephenson, CRJ | | | | Balachandran, R | | | | Raccor, BS | | | | Lu, Y | | | | Zhu, G | | | | Xie, W | | | | Wipf, P | pwipf@pitt.edu | PWIPF | | Day, BW | | | |
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Date: |
3 January 2005 |
Date Type: |
Publication |
Journal or Publication Title: |
Bioorganic and Medicinal Chemistry |
Volume: |
13 |
Number: |
1 |
Page Range: |
157 - 164 |
DOI or Unique Handle: |
10.1016/j.bmc.2004.09.048 |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0968-0896 |
MeSH Headings: |
Amides--chemistry; Amides--pharmacology; Cell Line; Cell Line, Tumor; Drug Screening Assays, Antitumor; Estrogen Receptor Modulators--chemistry; Estrogen Receptor Modulators--pharmacology; Genes, Reporter; Humans; Receptors, Estrogen--metabolism; Structure-Activity Relationship |
PubMed ID: |
15582460 |
Date Deposited: |
30 Jan 2014 17:03 |
Last Modified: |
02 Feb 2019 15:56 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/20392 |
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