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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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Supplementary files

Article information


Submitted
05 Jan 2019
Accepted
06 Feb 2019
First published
06 Feb 2019

Org. Biomol. Chem., 2019,17, 2448-2466
Article type
Paper
Author version available

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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