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

doi:10.1039/d2cc02784d

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

Chemistry and Environmental Science

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

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 language	English (US)
Pages (from-to)	8500-8503
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	61
DOIs	https://doi.org/10.1039/d2cc02784d
State	Published - Jul 1 2022

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d2cc02784d

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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.",

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T1 - Selective chlorination of iminosydnones for fast release of amide, sulfonamide and urea-containing drugs

AU - Feng, Minghao

AU - Madegard, Léa

AU - Riomet, Margaux

AU - Louis, Manon

AU - Champagne, Pier Alexandre

AU - Pieters, Grégory

AU - Audisio, Davide

AU - Taran, Frédéric

PY - 2022/7/1

Y1 - 2022/7/1

N2 - 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.

AB - 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.

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JO - Chemical Communications

JF - Chemical Communications

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ER -

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

Abstract

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