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

被引：7

作者：

Ryzhakov, Dmytro ^{[1
]}

Beillard, Audrey ^{[2
]}

Le Bideau, Franck ^{[1
]}

Al-Shuaeeb, Riyadh Ahmed Atto ^{[1
]}

Alami, Mouad ^{[1
]}

Bantreilejoc, Xavier ^{[2
,3
]}

Bonnemoy, Aurore ^{[4
]}

Gautier, Arnaud ^{[4
]}

Lamaty, Frederic ^{[2
]}

Messaoudi, Samir ^{[1
]}

机构：

[1] Univ Paris Saclay, BioCIS, CNRS, F-92290 Chatenay Malabry, France

[2] Univ Montpellier, ENSCM, CNRS, IBMM, Montpellier, France

[3] Inst Univ France IUF, Montpellier, France

[4] Univ Clermont Auvergne, ICCF, UMR 6296, CNRS, F-63000 Clermont Ferrand, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 09期

关键词：

Glycosides; Mechanochemistry; Migita crosscoupling; N-Heterocyclic carbenes; Palladium; N-HETEROCYCLIC CARBENES; METAL-COMPLEXES; SILVER(I)-CARBENE COMPLEXES; ANTICANCER ACTIVITY; CATALYTIC-ACTIVITY; NHC LIGANDS; CARBOHYDRATE; EFFICIENT; MECHANOCHEMISTRY; COORDINATION;

D O I：

10.1002/ejoc.202101499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 beta-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.

引用

页数：8

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