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Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides.


ABSTRACT: Three original derivatives of the cytotoxic betulinic acid 3-O-α-l-rhamnopyranoside featuring a monomethylated rhamnoside residue were synthesized. An improved catalytic procedure was involved to functionalize the O-3 position of the monosaccharide in a site-selective fashion. The cytotoxicity of the novel compounds was evaluated in vitro to highlight the moderate impact of carbohydrate monomethylation on the biological activity of betulinic acid 3-O-α-l-rhamnopyranoside.

SUBMITTER: Gormand P 

PROVIDER: S-EPMC10552092 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-<i>O</i>-α-l-Rhamnopyranosides.

Gormand Paul P   Pichette André A   Legault Jean J   Alsarraf Jérôme J  

ACS omega 20230922 39


Three original derivatives of the cytotoxic betulinic acid 3-<i>O</i>-α-l-rhamnopyranoside featuring a monomethylated rhamnoside residue were synthesized. An improved catalytic procedure was involved to functionalize the <i>O</i>-3 position of the monosaccharide in a site-selective fashion. The cytotoxicity of the novel compounds was evaluated in vitro to highlight the moderate impact of carbohydrate monomethylation on the biological activity of betulinic acid 3-<i>O</i>-α-l-rhamnopyranoside. ...[more]

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