Access to <sup>18</sup>F-labelled isoxazoles by ruthenium-promoted 1,3-dipolar cycloaddition of 4-[<sup>18</sup>F]fluoro-<i>N</i>-hydroxybenzimidoyl chloride with alkynes

  1. Roscales García, Silvia 1
  2. Kniess, Torsten 1
  1. 1 Institute of Radiopharmaceutical Cancer Research; Helmholtz-Zentrum Dresden-Rossendorf; Dresden Germany
Journal:
Journal of Labelled Compounds and Radiopharmaceuticals

ISSN: 1099-1344

Year of publication: 2019

Volume: 62

Issue: 8

Pages: 393-403

Type: Article

DOI: 10.1002/JLCR.3708 GOOGLE SCHOLAR lock_openOpen access editor

More publications in: Journal of Labelled Compounds and Radiopharmaceuticals

Sustainable development goals

Abstract

4-[18F]Fluoro-N-hydroxybenzimidoyl chloride (18FBIC), an 18F-labelled aromatic nitrile oxide, was developed as building block for Ru-promoted 1,3-dipolar cycloaddition with alkynes. 18FBIC is obtained in a one-pot synthesis in up to 84% radiochemical yield (RCY) starting from [18F]fluoride with 4-[18F]fluorobenzaldehyde (18FBA) and 4-[18F]fluorobenzaldehyde oxime (18FBAO) as intermediates, by reaction of 18FBAO with N-chlorosuccinimide (NCS). 18FBIC was found to be a suitable and stable synthon to give access to 18F-labelled 3,4-diarylsubstituted isoxazoles by [Cp*RuCl(cod)]-catalysed 1,3-dipolar cycloaddition with various alkynes. So the radiosynthesis of a fluorine-18–labelled COX-2 inhibitor [18F]1b, a close derivative of valdecoxib, was performed with 18FBIC and 1-ethynyl-4-(methylsulfonyl)benzene, providing [18F]1b in up to 40% RCY after purification in 85 minutes. The application of 18FBIC as a building block in the synthesis of 18F-labelled heterocycles will generally extend the portfolio of available PET radiotracers.

Bibliographic References

  • Moses, (2011), Nucl Instrum Methods Phys Res A, 648, pp. S236, 10.1016/j.nima.2010.11.092
  • Jacobson, (2015), Bioconjug Chem, 26, pp. 1, 10.1021/bc500475e
  • Born, (2017), Chem Soc Rev, 46, pp. 4709, 10.1039/C6CS00492J
  • Wängler, (2010), Curr Med Chem, 17, pp. 1092, 10.2174/092986710790820615
  • Meyer, (2016), Bioconjug Chem, 27, pp. 2791, 10.1021/acs.bioconjchem.6b00561
  • Jäger, (2003), Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, pp. 361, 10.1002/0471221902.ch6
  • Zlatopolskiy, (2012), Chem Commun, 48, pp. 7134, 10.1039/c2cc31335a
  • Laube, (2013), Molecules, 18, pp. 6311, 10.3390/molecules18066311
  • Toyokuni, (2005), Bioorg Med Chem Lett, 15, pp. 4699, 10.1016/j.bmcl.2005.07.065
  • Majo, (2005), Bioorg Med Chem Lett, 15, pp. 4268, 10.1016/j.bmcl.2005.06.080
  • Grecian, (2008), Angew Chem Int Ed, 47, pp. 8285, 10.1002/anie.200801920
  • Roscales, (2018), Med Chem Commun, 9, pp. 534, 10.1039/C7MD00575J
  • Wilson, (1990), J Label Compd Radiopharm, 28, pp. 1189, 10.1002/jlcr.2580281012
  • Hasumi, (2014), Bioorg Med Chem, 22, pp. 4162, 10.1016/j.bmc.2014.05.045
  • Richarz, (2014), Org Biomol Chem, 12, pp. 8094, 10.1039/C4OB01336K
  • Jawalekar, (2011), Chemical Comm, 47, pp. 3198, 10.1039/c0cc04646a
  • Zlatopolskiy, (2013), J Label Compd Radiopharm, 56, pp. S169
  • Krapf, (2015), J Label Compd Radiopharm, 58, pp. S17
  • Lopez, (2015), J Fluorine Chem, 176, pp. 121, 10.1016/j.jfluchem.2015.06.006
  • Brinkmann, (2007), Tetrahedron, 63, pp. 8413, 10.1016/j.tet.2007.06.033