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

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Gormand, Paul, Pichette, André, Legault, Jean, Alsarraf, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10552092/
https://www.ncbi.nlm.nih.gov/pubmed/37810724
http://dx.doi.org/10.1021/acsomega.3c04301
_version_ 1785115892038762496
author Gormand, Paul
Pichette, André
Legault, Jean
Alsarraf, Jérôme
author_facet Gormand, Paul
Pichette, André
Legault, Jean
Alsarraf, Jérôme
author_sort Gormand, Paul
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-10552092
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-105520922023-10-06 Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides Gormand, Paul Pichette, André Legault, Jean Alsarraf, Jérôme ACS Omega [Image: see text] 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. American Chemical Society 2023-09-22 /pmc/articles/PMC10552092/ /pubmed/37810724 http://dx.doi.org/10.1021/acsomega.3c04301 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Gormand, Paul
Pichette, André
Legault, Jean
Alsarraf, Jérôme
Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title_full Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title_fullStr Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title_full_unstemmed Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title_short Synthesis and Cytotoxicity of Monomethylated Betulinic Acid 3-O-α-l-Rhamnopyranosides
title_sort synthesis and cytotoxicity of monomethylated betulinic acid 3-o-α-l-rhamnopyranosides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10552092/
https://www.ncbi.nlm.nih.gov/pubmed/37810724
http://dx.doi.org/10.1021/acsomega.3c04301
work_keys_str_mv AT gormandpaul synthesisandcytotoxicityofmonomethylatedbetulinicacid3oalrhamnopyranosides
AT pichetteandre synthesisandcytotoxicityofmonomethylatedbetulinicacid3oalrhamnopyranosides
AT legaultjean synthesisandcytotoxicityofmonomethylatedbetulinicacid3oalrhamnopyranosides
AT alsarrafjerome synthesisandcytotoxicityofmonomethylatedbetulinicacid3oalrhamnopyranosides

Ejemplares similares