Selective chlorination of iminosydnones for fast release of amide, sulfonamide and urea-containing drugs

Minghao Feng, Léa Madegard, Margaux Riomet, Manon Louis, Pier Alexandre Champagne, Grégory Pieters, Davide Audisio, Frédéric Taran

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we describe a methodology for iminosydnone chlorination and we demonstrate the high beneficial effect of this modification on the reactivity of these mesoionic dipoles in strain-promoted cycloaddition reactions. Exploiting their reaction with cyclooctynes, we used these new iminosydnones for bioorthogonal release of amide, urea and sulfonamide containing drugs. Notably, drugs containing a terminal amide function were released for the first time with good kinetic constants.

Original languageEnglish (US)
JournalChemical Communications
DOIs
StateAccepted/In press - 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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