Cargando…

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

Ejemplares similares

Bidesmosidic betulin saponin bearing L-rhamnopyranoside moieties induces apoptosis and inhibition of lung cancer cells growth in vitro and in vivo
por: Mihoub, Mouadh, et al.
Publicado: (2018)

Synthesis, cytotoxicity and anti-inflammatory activity of rhamnose-containing ursolic and betulinic acid saponins
por: Sylla, Balla, et al.
Publicado: (2019)

Methyl 4-O-benzyl-α-l-rhamnopyranoside
por: Pendrill, Robert, et al.
Publicado: (2014)

Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives
por: Matin, Mohammed Mahbubul, et al.
Publicado: (2016)

4-Nitrophenyl α-l-rhamnopyranoside hemihydrate
por: Peltier, Pauline, et al.
Publicado: (2008)

4-Nitrophenyl α-l-rhamnopyranoside hemihydrate
por: Zhang, Jianbo, et al.
Publicado: (2008)

Hemisynthesis and Biological Evaluation of Cinnamylated, Benzylated, and Prenylated Dihydrochalcones from a Common Bio-Sourced Precursor
por: Ardaillou, Anne, et al.
Publicado: (2021)

Anti-Inflammatory, Antioxidant, Antibiotic, and Cytotoxic Activities of Tanacetum vulgare L. Essential Oil and Its Constituents
por: Coté, Héloïse, et al.
Publicado: (2017)

Hepatoprotective Effects of Kaempferol-3-O-α-l-Arabinopyranosyl-7-O-α-l-Rhamnopyranoside on d-Galactosamine and Lipopolysaccharide Caused Hepatic Failure in Mice
por: Dong, Lin, et al.
Publicado: (2017)

Immunomodulatory properties of quercetin-3-O-α-L-rhamnopyranoside from Rapanea melanophloeos against influenza a virus
por: Mehrbod, Parvaneh, et al.
Publicado: (2018)

Phenyl 2,3-O-isopropylidene-1-thio-α-d-rhamnopyranoside
por: Osman, Hasnah, et al.
Publicado: (2007)

Crystal structure of methyl α-l-rhamnopyranosyl-(1→2)-α-l-rhamnopyranoside monohydrate
por: Eriksson, Lars, et al.
Publicado: (2019)

Betulin Phosphonates; Synthesis, Structure, and Cytotoxic Activity
por: Chrobak, Elwira, et al.
Publicado: (2016)

Acaricidal Activity of Bufadienolides Isolated from Drimia pancration against Tetranychus urticae, and Structural Elucidation of Arenobufagin-3-O-α-L-rhamnopyranoside
por: Badalamenti, Natale, et al.
Publicado: (2022)

α-Mangostin Enhances Betulinic Acid Cytotoxicity and Inhibits Cisplatin Cytotoxicity on HCT 116 Colorectal Carcinoma Cells
por: Aisha, Abdalrahim F. A., et al.
Publicado: (2012)

New acetylenic derivatives of betulin and betulone, synthesis and cytotoxic activity
por: Bębenek, Ewa, et al.
Publicado: (2016)

Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin
por: Boryczka, Stanisław, et al.
Publicado: (2013)

Rhamnopyranoside-Based Fatty Acid Esters as Antimicrobials: Synthesis, Spectral Characterization, PASS, Antimicrobial, and Molecular Docking Studies
por: Sanaullah, Abul Fazal Muhammad, et al.
Publicado: (2023)

Catechin-7-O-α-L-rhamnopyranoside can reduce α-MSH-induced melanogenesis in B16F10 melanoma cells through competitive inhibition of tyrosinase
por: Hwang, Taehyeok, et al.
Publicado: (2022)

Cytotoxic Steroidal Saponins from the Flowers of Allium leucanthum
por: Mskhiladze, Lasha, et al.
Publicado: (2008)

Complete Genome Sequence of Streptomyces sp. TN58, a Producer of Acyl Alpha-l-Rhamnopyranosides
por: Najah, Soumaya, et al.
Publicado: (2017)

Synthesis of 2-Aminoethanesulfonamides of Betulinic and Betulonic Acids
por: Komissarova, N. G., et al.
Publicado: (2021)

Identification of a Selective PDE4B Inhibitor From Bryophyllum pinnatum by Target Fishing Study and In Vitro Evaluation of Quercetin 3-O-α-L-Arabinopyranosyl-(1→2)-O-α-L-Rhamnopyranoside
por: Lourenço, Estela M. G., et al.
Publicado: (2020)

High cytotoxicity of betulin towards fish and murine fibroblasts: Is betulin safe for nonneoplastic cells?
por: Małaczewska, Joanna, et al.
Publicado: (2021)

Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-l-rhamnopyranoside: a glycosyl acceptor
por: Tsai, Yow-Fu, et al.
Publicado: (2008)

Experimental validation and computational modeling of anti-influenza effects of quercetin-3-O-α-L-rhamnopyranoside from indigenous south African medicinal plant Rapanea melanophloeos
por: Mehrbod, Parvaneh, et al.
Publicado: (2019)

Ethylenediamine Derived Carboxamides of Betulinic and Ursolic Acid as Potential Cytotoxic Agents
por: Kahnt, Michael, et al.
Publicado: (2018)

The Biological Activity of Monarda didyma L. Essential Oil and Its Effect as a Diet Supplement in Mice and Broiler Chicken
por: Côté, Héloïse, et al.
Publicado: (2021)

Synthesis and Antiplasmodial Activity of Betulinic Acid and Ursolic Acid Analogues
por: Innocente, Adrine M., et al.
Publicado: (2012)

Synthesis and Pharmacological Effects of Diosgenin–Betulinic Acid Conjugates
por: Özdemir, Zülal, et al.
Publicado: (2020)

Phenolic Extract from Aralia nudicaulis L. Rhizomes Inhibits Cellular Oxidative Stresses
por: Lion, Quentin, et al.
Publicado: (2021)

Cytotoxic profiling of artesunic and betulinic acids and their synthetic hybrid compound on neurons and gliomas
por: Ackermann, Annemarie, et al.
Publicado: (2017)

Design, Synthesis and Preliminary Evaluation of the Cytotoxicity and Antibacterial Activity of Novel Triphenylphosphonium Derivatives of Betulin
por: Grymel, Mirosława, et al.
Publicado: (2022)

Design, synthesis and biological evaluation of novel betulinic acid derivatives
por: Yang, Shengjie, et al.
Publicado: (2012)

Chemical Strategies towards the Synthesis of Betulinic Acid and Its More Potent Antiprotozoal Analogues
por: Cunha, André Barreto, et al.
Publicado: (2021)

Increased betulinic acid induced cytotoxicity and radiosensitivity in glioma cells under hypoxic conditions
por: Bache, Matthias, et al.
Publicado: (2011)

Hypoxia Enhances the Antiglioma Cytotoxicity of B10, a Glycosylated Derivative of Betulinic Acid
por: Fischer, Sebastian, et al.
Publicado: (2014)

Pharmaco-Toxicological Assessment of the Combined Cytotoxic Effects of Digoxin and Betulinic Acid in Melanoma Cells
por: Rednic, Robert, et al.
Publicado: (2022)

Synthesis and Biological Evaluation of RGD and isoDGR–Monomethyl Auristatin Conjugates Targeting Integrin α(V)β(3)
por: Raposo Moreira Dias, André, et al.
Publicado: (2019)

Cytotoxic Effects of Alternariol, Alternariol Monomethyl-Ether, and Tenuazonic Acid and Their Relevant Combined Mixtures on Human Enterocytes and Hepatocytes
por: den Hollander, Danica, et al.
Publicado: (2022)

Cannot write session to /tmp/vufind_sessions/sess_p9itivajlofcgu6qso5nst7dcn