Azoliums and Ag(I)-N-Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity

Dmytro Ryzhakov; Audrey Beillard; Franck Le Bideau; Riyadh Ahmed Atto Al-Shuaeeb; Mouad Alami; Xavier Bantreil; Aurore Bonnemoy; Arnaud Gautier; Frédéric Lamaty; Samir Messaoudi

doi:10.1002/ejoc.202101499

Azoliums and Ag(I)-N-Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity

Dmytro Ryzhakov
, Audrey Beillard
, Franck Le Bideau
, Riyadh Ahmed Atto Al-Shuaeeb
, Mouad Alami
, Xavier Bantreil
, Aurore Bonnemoy
, Arnaud Gautier
, Frédéric Lamaty
, Samir Messaoudi

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

Abstract

A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3-catalyzed Migita cross-coupling between p-di-iodo azoliums and protected or unprotected β-1-thioglucose partners. Moreover, a solvent-free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)-N-heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)-NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate-based N-heterocyclic derivatives.

Original language	English
Article number	e202101499
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.202101499
Publication status	Published - 7 Mar 2022
Externally published	Yes

Keywords

Glycosides
Mechanochemistry
Migita cross-coupling
N-Heterocyclic carbenes
Palladium

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10.1002/ejoc.202101499

Cite this

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title = "Azoliums and Ag(I)-N-Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity",

abstract = "A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3-catalyzed Migita cross-coupling between p-di-iodo azoliums and protected or unprotected β-1-thioglucose partners. Moreover, a solvent-free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)-N-heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)-NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate-based N-heterocyclic derivatives.",

keywords = "Glycosides, Mechanochemistry, Migita cross-coupling, N-Heterocyclic carbenes, Palladium",

author = "Dmytro Ryzhakov and Audrey Beillard and \{Le Bideau\}, Franck and Al-Shuaeeb, \{Riyadh Ahmed Atto\} and Mouad Alami and Xavier Bantreil and Aurore Bonnemoy and Arnaud Gautier and Fr{\'e}d{\'e}ric Lamaty and Samir Messaoudi",

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year = "2022",

month = mar,

day = "7",

doi = "10.1002/ejoc.202101499",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "9",

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TY - JOUR

T1 - Azoliums and Ag(I)-N-Heterocyclic Carbene Thioglycosides

T2 - Synthesis, Reactivity and Bioactivity

AU - Ryzhakov, Dmytro

AU - Beillard, Audrey

AU - Le Bideau, Franck

AU - Al-Shuaeeb, Riyadh Ahmed Atto

AU - Alami, Mouad

AU - Bantreil, Xavier

AU - Bonnemoy, Aurore

AU - Gautier, Arnaud

AU - Lamaty, Frédéric

AU - Messaoudi, Samir

PY - 2022/3/7

Y1 - 2022/3/7

N2 - A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3-catalyzed Migita cross-coupling between p-di-iodo azoliums and protected or unprotected β-1-thioglucose partners. Moreover, a solvent-free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)-N-heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)-NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate-based N-heterocyclic derivatives.

AB - A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3-catalyzed Migita cross-coupling between p-di-iodo azoliums and protected or unprotected β-1-thioglucose partners. Moreover, a solvent-free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)-N-heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)-NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate-based N-heterocyclic derivatives.

KW - Glycosides

KW - Mechanochemistry

KW - Migita cross-coupling

KW - N-Heterocyclic carbenes

KW - Palladium

U2 - 10.1002/ejoc.202101499

DO - 10.1002/ejoc.202101499

M3 - Article

AN - SCOPUS:85124763677

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

M1 - e202101499

ER -

Azoliums and Ag(I)-N-Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity

Abstract

Keywords

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