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Preparation of selectively protected protoescigenin derivatives for synthesis of escin analogs and neoglycoconjugates

100%

Jatczak K., Gruza M., Filip K., Cmoch P., Grynkiewicz G.

Open Chemistry

2014

vol. 12

issue 12

1222-1231

Protoescigenin, the main aglycone of horse chestnut saponin mixture known as escin, was selected as substrate for exploratory chemistry towards selective protection, followed by propargyl ether formation and subsequent condensation with azido-monosaccharides, to obtain novel triazole linked conjugates of the triterpene.

Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity

88%

Rjabova J., Rjabovs V., Moreno Vargas A., Clavijo E., Turks M.

Open Chemistry

2012

vol. 10

issue 2

386-394

Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These new compounds are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by the presence of a methylene linker (-CH2-) between the C(3) of allose and the triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-d-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-d-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration. [...]

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2 Open Chemistry

1 2014

1 2012

1 Clavijo E.

1 Cmoch P.

1 Filip K.

1 Gruza M.

1 Grynkiewicz G.

1 Jatczak K.

1 Moreno Vargas A.

1 Rjabova J.

1 Rjabovs V.

1 Turks M.

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Preparation of selectively protected protoescigenin derivatives for synthesis of escin analogs and neoglycoconjugates

Synthesis of novel 3-deoxy-3-C-triazolylmethyl-allose derivatives and evaluation of their biological activity