Arabinogalactan propargyl ethers in the A 3 -coupling reaction with aldehydes and secondary cyclic amines.

Autor: Grishchenko LA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation., Parshina LN; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation., Larina LI; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation., Belovezhetz LA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation., Trofimov BA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation. Electronic address: boris_trofimov@irioch.irk.ru.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2023 Jan 15; Vol. 300, pp. 120239. Date of Electronic Publication: 2022 Oct 20.
DOI: 10.1016/j.carbpol.2022.120239
Abstrakt: A family of novel pharmacologically prospective carbohydrate polymer aminomethylpropargyl derivatives has been synthesized by CuI-catalyzed A 3 -coupling reaction of arabinogalactan propargyl ethers with aldehydes and secondary amines in DMSO at 23-65 °С. The arabinogalactan derivatives bearing phenyl, pyridinе, and furan moieties in combination with piperidyne, pyrrolidyne, morpholine fragments are prepared in up to 95 % yield and 0.3-2.0 degree of substitution. Conversion of the propargyl groups of the starting arabinogalactan ethers reaches in most cases 80-100 %. The non-catalyzed aminoalkylation (96-100 °С, degree of substitution up to 1.1) of propargylated AG proceeds both at the ethynyl and hydroxy centers to afford mainly the products of C-substitution. Some of the synthesized compounds and their hydrochlorination products show the pronounced bacteriostatic activity with respect to Gram-negative microorganism.
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2022 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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