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

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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Janjic, JM
Mu, Y
Kendall, C
Stephenson, CRJ
Balachandran, R
Raccor, BS
Lu, Y
Zhu, G
Xie, W
Wipf, Ppwipf@pitt.eduPWIPF
Day, BW
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.pitt.edu/id/eprint/20392

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