eprintid: 20425
rev_number: 24
userid: 1419
dir: disk0/00/02/04/25
datestamp: 2014-01-30 17:01:32
lastmod: 2021-06-12 22:55:55
status_changed: 2014-01-30 17:01:32
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Wipf, P
creators_name: Lynch, SM
creators_name: Birmingham, A
creators_name: Tamayo, G
creators_name: Jiménez, A
creators_name: Campos, N
creators_name: Powis, G
creators_email: pwipf@pitt.edu
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creators_id: PWIPF
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title: Natural product based inhibitors of the thioredoxin-thioredoxin reductase system
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
abstract: Spiroketal naphthodecalins are readily assembled by Barton's base mediated Ullmann binaphthyl ether coupling, Dakin reactions and hypervalent iodine spirocyclization. The core structures can be further diversified by enone addition and Stille coupling reactions. Nanomolar inhibitors for the Trx/TrxR redox control system were prepared by this approach and compared to series of natural product isolates. Cytotoxicity in MCF-7 cell assays ranged from an IC50 of 1.6 to > 100 μM.
date: 2004-06-07
date_type: published
publication: Organic and Biomolecular Chemistry
volume: 2
number: 11
pagerange: 1651 - 1658
refereed: TRUE
issn: 1477-0520
id_number: 10.1039/b402431a
pmid: 15162219
mesh_headings: Antineoplastic Agents--chemistry
mesh_headings: Antineoplastic Agents--pharmacology
mesh_headings: Cell Line, Tumor
mesh_headings: Drug Screening Assays, Antitumor
mesh_headings: Enzyme Inhibitors--chemistry
mesh_headings: Enzyme Inhibitors--pharmacology
mesh_headings: Humans
mesh_headings: Inhibitory Concentration 50
mesh_headings: Molecular Structure
mesh_headings: Naphthoquinones--chemistry
mesh_headings: Naphthoquinones--pharmacology
mesh_headings: Spiro Compounds--chemistry
mesh_headings: Spiro Compounds--pharmacology
mesh_headings: Thioredoxin-Disulfide Reductase--antagonists & inhibitors
mesh_headings: Thioredoxins--antagonists & inhibitors
chemical_names: Antineoplastic Agents
chemical_names: Enzyme Inhibitors
chemical_names: Naphthoquinones
chemical_names: Spiro Compounds
chemical_names: Thioredoxins
chemical_names: Thioredoxin-Disulfide Reductase
citation:   Wipf, P and Lynch, SM and Birmingham, A and Tamayo, G and Jiménez, A and Campos, N and Powis, G  (2004) Natural product based inhibitors of the thioredoxin-thioredoxin reductase system.  Organic and Biomolecular Chemistry, 2 (11).  1651 - 1658.  ISSN 1477-0520     
document_url: http://d-scholarship-dev.library.pitt.edu/20425/1/licence.txt