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

共 50 条

[31] 4-Vinylbenzyl-substituted silver(I) N-heterocyclic carbene complexes and ruthenium(II) N-heterocyclic carbene complexes: synthesis and transfer hydrogenation of ketones
Aktas, Aydin
Gok, Yetkin
TRANSITION METAL CHEMISTRY, 2014, 39 (08) : 925 - 931
[32] Exploring the Reactivity and Biological Effects of Heteroleptic N-Heterocyclic Carbene Gold(I)-Alkynyl Complexes
Oberkofler, Jens
Aikman, Brech
Bonsignore, Riccardo
Poethig, Alexander
Platts, James
Casini, Angela
Kuehn, Fritz E.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (11-12) : 1040 - 1051
[33] Novel nonsymmetrically benzimidazolium salts and their silver (I)-N-heterocyclic carbene complexes: Synthesis, DFT study and Anticancer activities
Rahali, Emna
Boubakri, Lamia
Gurbuz, Nevin
Ozdemir, Ismail
Mansour, Lamjed
Arfaoui, Youssef
Sauthier, Mathieu
Hamdi, Naceur
JOURNAL OF MOLECULAR STRUCTURE, 2025, 1321
[34] Synthesis, characterization, and coordination chemistry of a phenanthridine-containing N-heterocyclic carbene ligand
Mondal, Rajarshi
Ortiz, Robert J.
Braun, Jason D.
Herbert, David E.
CANADIAN JOURNAL OF CHEMISTRY, 2021, 99 (02) : 245 - 252
[35] Synthesis, characterization, and investigation of antiproliferative activity of novel Ag (I)-N-Heterocyclic Carbene (NHC) compounds
Cevik-Yildiz, Esranur
Sahin, Neslihan
Sahin-Bolukbasi, Serap
JOURNAL OF MOLECULAR STRUCTURE, 2020, 1199
[36] N-heterocyclic carbene enabled synthesis of conjugated polymers
Suzuki, Yasuo
Ono, Robert J.
Ueda, Mitsuru
Bielawski, Christopher W.
EUROPEAN POLYMER JOURNAL, 2013, 49 (12) : 4276 - 4280
[37] A Convenient Approach for the Synthesis of Multidentate N-Heterocyclic Carbene Ligand Precursors
Kumar Meher, Naresh
Kashyap, Anubhab
Geetharani, K.
CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (01)
[38] Synthesis and characterization of an N-heterocyclic carbene palladium-based complex
Arslan, Hakan
VanDerveer, Don
Demir, Serpil
Ozdemir, Ismail
Cetinkaya, Bekir
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 : C404 - C405
[39] Synthesis and Reactivity of an Aluminium N-heterocyclic Aminal
Wilde, Taylor
Murphy, Fainche
Smylie, Cooper R. T.
Kennedy, Alan R.
Weetman, Catherine E.
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (05)
[40] Stable Radical Cation and Dication of an N-Heterocyclic Carbene Stabilized Digallene: Synthesis, Characterization and Reactivity
Feng, Zhongtao
Fang, Yong
Ruan, Huapeng
Zhao, Yue
Tan, Gengwen
Wang, Xinping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (17) : 6769 - 6774

← 1 2 3 4 5 →