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Issue 9, 2019
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In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors

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Abstract

A continuous flow photooxygenation of 7-aminothieno[3,2-c]pyridin-4(5H)-ones to produce 7-iminothieno[3,2-c]pyridine-4,6(5H,7H)-diones has been developed, utilizing ambient air as the sole reactant. N-H Imines are formed as the major products, and excellent functional group tolerance and conversion on gram-scale without the need for chromatographic purification allow for facile late-stage diversification of the aminothienopyridinone scaffold. Several analogs exhibit potent in vitro inhibition of the cancer-associated protein tyrosine phosphatase PTP4A3, and the SAR supports an exploratory docking model.

Graphical abstract: In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors

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Publication details

The article was received on 05 Jan 2019, accepted on 06 Feb 2019 and first published on 06 Feb 2019


Article type: Paper
DOI: 10.1039/C9OB00025A
Citation: Org. Biomol. Chem., 2019,17, 2448-2466

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    In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors

    N. R. Tasker, E. J. Rastelli, I. K. Blanco, J. C. Burnett, E. R. Sharlow, J. S. Lazo and P. Wipf, Org. Biomol. Chem., 2019, 17, 2448
    DOI: 10.1039/C9OB00025A

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