- In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors
-
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.
- Tasker, Nikhil R.,Rastelli, Ettore J.,Blanco, Isabella K.,Burnett, James C.,Sharlow, Elizabeth R.,Lazo, John S.,Wipf, Peter
-
supporting information
p. 2448 - 2466
(2019/03/06)
-
- Photooxygenation of an amino-thienopyridone yields a more potent PTP4A3 inhibitor
-
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 thienopyrid
- Salamoun, Joseph M.,McQueeney, Kelley E.,Patil, Kalyani,Geib, Steven J.,Sharlow, Elizabeth R.,Lazo, John S.,Wipf, Peter
-
supporting information
p. 6398 - 6402
(2016/07/16)
-