172340-63-5

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 172340-62-4 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-(β-D-galactopyranosyloxy)-4-octadecene 
• 103348-50-1 (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 118711-43-6 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy]-4-octadecene 
• 172340-47-5 (2S,3R,4E)-2-azido-3-(benzoyloxy)-1-(β-D-galactopyranosyloxy)-4-octadecene 
• 1053247-80-5 Benzoic acid (E)-(R)-1-[(S)-1-amino-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 

Downstream Products

• 194299-23-5 (2S,3R,4E)-2-(hexadecanoylamino)-3-(benzoyloxy)-1-[(3,4-O-isopropylidene-6-O-pivaloyl-β-D-galactopyranosyl)oxy]-4-octadecene 

Relevant academic research and scientific papers

Sulfated galactocerebrosides as potential antiinflammatory agents

Native sulfatides, as well as many sulfated glycolipids, have been shown to avidly bind to the selectin receptors. In vivo, native sulfatides significantly block activity in selectin-dependent inflammatory responses. The fact that nonsulfated galactocerebrosides did not inhibit selectin- mediated adhesion identified a critical role for the anionic sulfate residue. We therefore initiated a program to evaluate the activity of position isomers. This study showed a binding selectivity for the positions 2 and 3 of the sulfate group on the carbohydrate ring as well as enhanced activity for the disulfated analogs. Furthermore, it was discovered that the attachment of lipophilic substituents on the carbohydrate ring was tolerated, consistent with the presence of a lipophilic pocket in the binding cavity. This resulted in compounds with a 6-fold increased potency.

Sulfated β-glycolipid derivatives as cell adhesion inhibitors

There is provided novel sulfated p-glycolipid compounds of the formula STR1 wherein R is an acyl residue of a fatty acid; R1 is --(CH=CH)m --(CH2)n --CH3 ; R2, R3, R4 and R6 each are independently --SO3 H, hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C1-4 alkyl, trifluoromethyl, hydroxy and C1-4 alkoxy; or R4 and R6, taken together are isopropylidene; provided at least two of R2, R3, R4 and R6 are --SO3 H; R5 is hydrogen, unsubstituted or substituted alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C1-4 alkyl, trifluoromethyl, hydroxy and C1-4 alkoxy; m is an integer of 0 or 1; n is an integer of from 5 to 14, inclusive; or a non-toxic pharmaceutically acceptable salt, solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.