Arabinogalactan propargyl ethers: Au-catalysed hydroamination by imidazols.

Autor: Grishchenko LA; A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky Str., 664033, Irkutsk, Russia., Parshina LN; A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky Str., 664033, Irkutsk, Russia., Larina LI; A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky Str., 664033, Irkutsk, Russia., Belovezhets LA; A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky Str., 664033, Irkutsk, Russia., Klimenkov IV; Limnological Institute, Siberian Branch, Russian Academy of Sciences, 3, Ulan-Batorskaya Str., 664033, Irkutsk, Russia., Ustinov AY; Institute of Chemistry, Far East Branch, Russian Academy of Sciences, 159, Prosp. 100-letiya Vladivostoka, 690022, Vladivostok, Russia., Trofimov BA; A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1, Favorsky Str., 664033, Irkutsk, Russia. Electronic address: boris_trofimov@irioch.irk.ru.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2020 Oct 15; Vol. 246, pp. 116638. Date of Electronic Publication: 2020 Jun 13.
DOI: 10.1016/j.carbpol.2020.116638
Abstrakt: 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% HAuC1 4 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.
(Copyright © 2020 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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