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Issue 27, 2016
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Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

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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.

Graphical abstract: Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

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Publication details

The article was received on 30 Apr 2016, accepted on 07 Jun 2016 and first published on 07 Jun 2016


Article type: Communication
DOI: 10.1039/C6OB00946H
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 6398-6402
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    Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor

    J. M. Salamoun, K. E. McQueeney, K. Patil, S. J. Geib, E. R. Sharlow, J. S. Lazo and P. Wipf, Org. Biomol. Chem., 2016, 14, 6398
    DOI: 10.1039/C6OB00946H

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