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Synthesis of AX7593, a quinazoline-derived photoaffinity probe for EGFR.

[structure: see text] The synthesis of a photoaffinity probe for EGFR is described. O-Alkylation of 4-(meta-azidoanilino)-6-methoxy-7-hydroxy-quinazoline with a protected tetraethyleneglycol linker followed by the attachment of tetramethylrhodamine yielded the fluorescent probe AX7593. Photoaffinity labeling of EGFR by AX7593 (K(b) = 280 nM) was shown to have an efficiency of 34% and to be competitive with the EGFR inhibitors PP2 and AG1478.[1]

References

  1. Synthesis of AX7593, a quinazoline-derived photoaffinity probe for EGFR. Shreder, K.R., Wong, M.S., Nomanbhoy, T., Leventhal, P.S., Fuller, S.R. Org. Lett. (2004) [Pubmed]
 
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