Issue 27, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
30 Apr 2016
Accepted
07 Jun 2016
First published
07 Jun 2016

Org. Biomol. Chem., 2016,14, 6398-6402

Author version available

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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