112289-49-3Relevant academic research and scientific papers
The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals
Hamala, Vojtěch,?ervenková ??astná, Lucie,Kurfi?t, Martin,Cu?ínová, Petra,Balouch, Martin,Hrstka, Roman,Voňka, Petr,Karban, Jind?ich
supporting information, p. 4497 - 4506 (2021/05/31)
Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.
FLUORINATED CARBOHYDRATES AS POTENTIAL PLASMA MEMBRANE MODIFIERS AND INHIBITORS. SYNTHESIS OF 2-ACETAMIDO-2,6-DIDEOXY-6-FLUORO-D-GALACTOSE
Sharma, Moheswar,Potti, Gopalan G.,Simmons, Onda D.,Korytnyk, Walter
, p. 41 - 52 (2007/10/02)
Reaction of benzyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-mesyl-α-D-galactopyranoside with cesium fluoride gave benzyl 2-acetamido-3,6-anhydro-4-O-benzyl-2-deoxy-α-D-galactopyranoside instead of the desired 6-fluoro derivative.Acetonation of benzyl 2-ace
