Synthesis of 6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline: Aprospective irreversible EGFR binding probe

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Acrylamido-quinazolines substituted at the 6-position bindirreversibly to the intracellular ATP binding domain of the epidermalgrowth factor receptor (EGFR). A general route was developed forpreparing 6-substituted-4-anilinoquinazolines from [18F]fluoroanilinesfor evaluation as EGFR targeting agents with PET. By a cyclizationreaction, 2-[18F]fluoroaniline was reacted withN'-(2-cyano-4-nitrophenyl)-N,N-dimethylimidoformamide to produce6-nitro-4-(2-[18F]fluoroanilino)quinazoline in 27.5 percentdecay-corrected radiochemical yield. Acid mediated tin chloride reductionof the nitro group was achieved in 5 min (80 percent conversion) andsubsequent acylation with acrylic acid gave6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline in 8.5 percentdecay-corrected radiochemical yield, from starting fluoride, in less than2 hours.

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Vasdev, Neil; Dorff, Peter N.; Gibbs, Andrew R.; Nandanan,Erathodiyil; Reid, Leanne M.; O'Neil, James P. et al. March 30, 2004.

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Acrylamido-quinazolines substituted at the 6-position bindirreversibly to the intracellular ATP binding domain of the epidermalgrowth factor receptor (EGFR). A general route was developed forpreparing 6-substituted-4-anilinoquinazolines from [18F]fluoroanilinesfor evaluation as EGFR targeting agents with PET. By a cyclizationreaction, 2-[18F]fluoroaniline was reacted withN'-(2-cyano-4-nitrophenyl)-N,N-dimethylimidoformamide to produce6-nitro-4-(2-[18F]fluoroanilino)quinazoline in 27.5 percentdecay-corrected radiochemical yield. Acid mediated tin chloride reductionof the nitro group was achieved in 5 min (80 percent conversion) andsubsequent acylation with acrylic acid gave6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline in 8.5 percentdecay-corrected radiochemical yield, from starting fluoride, in less than2 hours.

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  • Journal Name: Journal of Labelled Compounds andRadiopharmaceuticals; Journal Volume: 48; Journal Issue: 2; Related Information: Journal Publication Date: February2005

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  • Report No.: LBNL--58512
  • Grant Number: DE-AC02-05CH11231
  • Grant Number: NIHCA94253
  • Office of Scientific & Technical Information Report Number: 882913
  • Grant Number: CA94253
  • Archival Resource Key: ark:/67531/metadc892764

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  • March 30, 2004

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  • Sept. 23, 2016, 2:42 p.m.

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  • Nov. 28, 2017, 8:12 p.m.

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Vasdev, Neil; Dorff, Peter N.; Gibbs, Andrew R.; Nandanan,Erathodiyil; Reid, Leanne M.; O'Neil, James P. et al. Synthesis of 6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline: Aprospective irreversible EGFR binding probe, article, March 30, 2004; Berkeley, California. (digital.library.unt.edu/ark:/67531/metadc892764/: accessed July 23, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.