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.
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页数：8
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