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.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Amination
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Enzyme Inhibitors / chemistry*
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Enzyme Inhibitors / pharmacology*
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Humans
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Light
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Models, Molecular
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Neoplasm Proteins / antagonists & inhibitors*
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Neoplasm Proteins / metabolism
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Oxidation-Reduction
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Protein Tyrosine Phosphatases / antagonists & inhibitors*
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Protein Tyrosine Phosphatases / metabolism
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Pyridones / chemistry*
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Pyridones / pharmacology*
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Structure-Activity Relationship
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Thienopyridines / chemistry*
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Thienopyridines / pharmacology*
Substances
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Enzyme Inhibitors
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Neoplasm Proteins
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Pyridones
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Thienopyridines
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PTP4A3 protein, human
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Protein Tyrosine Phosphatases