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Natural product based inhibitors of the thioredoxin-thioredoxin reductase system

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

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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.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Lynch, SM
Birmingham, A
Tamayo, G
Jiménez, A
Campos, N
Powis, G
Date: 7 June 2004
Date Type: Publication
Journal or Publication Title: Organic and Biomolecular Chemistry
Volume: 2
Number: 11
Page Range: 1651 - 1658
DOI or Unique Handle: 10.1039/b402431a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1477-0520
MeSH Headings: Antineoplastic Agents--chemistry; Antineoplastic Agents--pharmacology; Cell Line, Tumor; Drug Screening Assays, Antitumor; Enzyme Inhibitors--chemistry; Enzyme Inhibitors--pharmacology; Humans; Inhibitory Concentration 50; Molecular Structure; Naphthoquinones--chemistry; Naphthoquinones--pharmacology; Spiro Compounds--chemistry; Spiro Compounds--pharmacology; Thioredoxin-Disulfide Reductase--antagonists & inhibitors; Thioredoxins--antagonists & inhibitors
PubMed ID: 15162219
Date Deposited: 30 Jan 2014 17:01
Last Modified: 22 Jun 2021 12:55


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