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Org Biomol Chem. 2016 Jul 6;14(27):6398-402. doi: 10.1039/c6ob00946h.

Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor.

Author information

1
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf@pitt.edu.
2
Department of Pharmacology, University of Virginia, Charlottesville, Virginia 22908, USA. lazo@virginia.edu ers7g@virginia.edu.

Abstract

The phosphatase PTP4A3 is an attractive anticancer target, but knowledge of its exact role in cells remains incomplete. A potent, structurally novel inhibitor of the PTP4A family was obtained by photooxygenation of a less active, electron-rich thienopyridone (1). Iminothienopyridinedione 13 displays increased solution stability and is readily obtained by two new synthetic routes that converge in the preparation of 1. The late-stage photooxygenation of 1 to give 13 in high yield highlights the potential of this reaction to modify the structure and properties of a biological lead compound and generate value for expanding the scope of an SAR investigation. Analog 13 should become a valuable tool for further exploration of the role of PTP4A3 in tumor progression.

PMID:
27291491
PMCID:
PMC4935606
DOI:
10.1039/c6ob00946h
[Indexed for MEDLINE]
Free PMC Article

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