64697-82-1

Upstream product

• 131591-67-8 (3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester 
• 84708-52-1 [(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-acetic acid ethyl ester 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 61865-36-9 (-)-1,2:5,6-Di-O-isopropylidene-3-O-(ethoxycarbonyl)methyl-α-D-glucofuranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Downstream Products

• 139010-08-5 N²-<(1,2-O-isopropylidene-α-D-glucofuranos-3-O-yl)acetyl>-L-lysin-4-acetamidoanilide 4-toluenesulfonate 
• 84708-56-5 Benzyl N-<(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranos-3-O-yl)acetyl>-L-alaninate 

Relevant academic research and scientific papers

Synthesis and anti-HIV activity of glucose-containing prodrugs derived from saquinavir, indinavir and nelfinavir

With the aim at improving the transport of the current HIV protease inhibitors across the intestinal and blood brain barriers and their penetration into the central nervous system, the synthesis of various acyl and carbamatoyl glucose-containing prodrugs derived from saquinavir, indinavir and nelfinavir, their in vitro stability with respect to hydrolysis, and their anti-HIV activity have been investigated. D-Glucose, which is actively transported across these barriers, was connected through its 3-hydroxyl to these antiproteases via a linker. The liberation of the active free drug during the incubation time of the prodrugs with the cells was found to be crucial for HIV inhibition. The labile ester linking of the glucose-containing moiety to the peptidomimetic hydroxyl of saquinavir or to the indinavir C-8 hydroxyl, which is not part of the transition state isostere, is not an obstacle for anti-HIV activity. This is not the case for its stable carbamate linking to the peptidomimetic hydroxyl of saquinavir, indinavir and nelfinavir. The chemical stability with respect to hydrolysis of some of the saquinavir and indinavir prodrugs reported here, the liberation rate of the active free drug and the HIV inhibitory potency are acceptable for an in vivo use of these prodrugs. These glucose-linked ester and carbamate prodrugs display a promising therapeutic potential provided that their bioavailability, penetration into the HIV sanctuaries, and/or the liberation of the active free drug from the carbamate prodrugs are improved. Furthermore, no cytotoxicity was detected for the prodrugs for concentrations as high as 10 or even 100 μM, thus indicating an encouraging therapeutic index.

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

Versatile approaches to sugar amino acid building blocks as precursors of glycopeptides

The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length o

4-Acetamidophenyl esters and 4-acetamidoanilides of L-arginine,p-guanidino-L-phenylalanine, L-lysine, N2-[D-fructos-3-O-yl and D-glucos-3-O-yl]acetyl-L-lysine as potential acrosin inhibitors

Syntheses of4-acetamidophenyl esters and 4-acetamidoanilides of L-lysine,p-guanidino-L-phenylalanine,L-leucyl-L-lysine, L-leucyl-L-leucyl-L-lysine, N 2-[(1-2-O-isopropylidene-α-D-glucofuranos-3-O-yl)acetyl]-L- rysine, N 2-[(1,2-O-iso

The Synthesis of N--L-alanine and N--L-alanine

N--L-alanine (7a) was synthesized, which has a glucose residue instead of N-acetylglucosamine residue in the muramyl peptide. N--L-alanine (7b) was also synthesized as a glycolyl analog of 7a in order