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

Authors

Minghao Feng, Université Paris-Saclay
Léa Madegard, Université Paris-Saclay
Margaux Riomet, Université Paris-Saclay
Manon Louis, Université Paris-Saclay
Pier Alexandre Champagne, New Jersey Institute of Technology
Grégory Pieters, Université Paris-Saclay
Davide Audisio, Université Paris-Saclay
Frédéric Taran, Université Paris-Saclay

Document Type

Article

Publication Date

7-1-2022

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.

Identifier

85133840469 (Scopus)

Publication Title

Chemical Communications

External Full Text Location

https://doi.org/10.1039/d2cc02784d

e-ISSN

1364548X

ISSN

13597345

PubMed ID

35797662

First Page

8500

Last Page

8503

Issue

61

Volume

58

Recommended Citation

Feng, Minghao; Madegard, Léa; Riomet, Margaux; Louis, Manon; Champagne, Pier Alexandre; Pieters, Grégory; Audisio, Davide; and Taran, Frédéric, "Selective chlorination of iminosydnones for fast release of amide, sulfonamide and urea-containing drugs" (2022). Faculty Publications. 2843.
https://digitalcommons.njit.edu/fac_pubs/2843