Arabinogalactan propargyl ethers: Au-catalysed hydroamination by imidazols

•Gold-catalyzed addition of imidazole molecules to arabinogalactan propargyl ether.•The degree of substitution by N-alkenylimidazole moieties reaches 1.6.•Reaction accompanies by reduction of Au(III) to Au(I)/Au(0).•Hydrochlorides of Au-arabinogalactan derivatives show high antibacterial activity. A...

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Published in:Carbohydrate polymers 2020-10, Vol.246, p.116638-116638, Article 116638
Main Authors: Grishchenko, Lyudmila A., Parshina, Lidiya N., Larina, Lyudmila I., Belovezhets, Lyudmila A., Klimenkov, Igor V., Ustinov, Alexander Yu, Trofimov, Boris A.
Format: Article
Language:English
Subjects:
Antimicrobial activity
Arabinogalactan functionalization
Gold-catalysis
Hydroamination
Imidazole derivatives
XPS study
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Summary:•Gold-catalyzed addition of imidazole molecules to arabinogalactan propargyl ether.•The degree of substitution by N-alkenylimidazole moieties reaches 1.6.•Reaction accompanies by reduction of Au(III) to Au(I)/Au(0).•Hydrochlorides of Au-arabinogalactan derivatives show high antibacterial activity. A method for the synthesis of pharmacologically prospective arabinogalactan (AG) imidazole- and benzimidazole derivatives in a yield of up to 97 % via Au(III)-catalyzed hydroamination of AG propargyl ethers has been developed. It is found that in the presence of 5 mol% HAuC14 and 10-fold excess imidazole relative to the propargyl groups, the hydroamination successfully competes with cross-linking processes to afford products soluble in DMSO and aqueous HC1 solutions (degree of substitution of imidazolylpropenyl fragments 0.5–1.8, yield 62–97 %). It is established that under the conditions of hydroamination Au(III) is reduced to give mainly Au(0) and minor amounts of Au(I), which are contained in AG imidazole derivatives as particles of 190−640 nm in size. Hydrochlorides of Au-containing AG imidazole derivatives show high bacteriostatic activity with respect to test gram-positive microorganisms and thus confirming their prospects as new AG-derived bioactive agents.
ISSN:0144-8617
1879-1344
DOI:10.1016/j.carbpol.2020.116638