31909-80-5

Upstream product

• 32742-31-7 p-Phenylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 92-69-3 4-Phenylphenol 
• 604-69-3 β-D-glucose pentaacetate 
• 134698-98-9 p-phenylphenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 1415483-55-4 biphenyl-4-yl 3-O-benzyl-α-D-mannopyranoside 
• 1415481-61-6 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside 
• 1415481-47-8 biphenyl-4-yl 4,6-O-benzylidene-α-D-mannopyranoside 
• 1415481-51-4 biphenyl-4-yl 2,4,6-tri-O-benzoyl-3-O-benzyl-α-D-mannopyranoside 
• 1415481-64-9 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-(phosphonooxy)methyl-α-D-mannopyranoside 
• 1415481-63-8 biphenyl-4-yl 2,3,4-tri-O-benzoyl-6-O-(methylthiomethyl)-α-D-mannopyranoside 
• 1415481-62-7 biphenyl-4-yl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 1415481-59-2 (biphenyl-4-yl 2,3-O-dibenzoyl-α-D-mannopyranoside) 4-phosphate 
• 1415481-58-1 biphenyl-4-yl 4-O-(dibenzyloxyphosphoryl)-2,3-di-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 
• 1415481-57-0 biphenyl-4-yl 2,3-di-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 
• 1415481-56-9 biphenyl-4-yl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 

Relevant academic research and scientific papers

MANNOSE PHOSPHATE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION

Compounds of the formula (I) (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are, independent of each other, hydrogen or a substituent as described in the specification, and one of RA, RB, RC and RD is P02(OH)2 and the other ones are hydrogen; are orally available medicaments useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating urinary tract infections.

Structure-based drug design and optimization of mannoside bacterial fimH antagonists

FimH-mediated cellular adhesion to mannosylated proteins is critical in the ability of uropathogenic E. coli (UPEC) to colonize and invade the bladder epithelium during urinary tract infection. We describe the discovery and optimization of potent small-molecule FimH bacterial adhesion antagonists based on α-d-mannose 1-position anomeric glycosides using X-ray structure-guided drug design. Optimized biarylmannosides display low nanomolar binding affinity for FimH in a fluorescence polarization assay and submicromolar cellular activity in a hemagglutination (HA) functional cell assay of bacterial adhesion. X-ray crystallography demonstrates that the biphenyl moiety makes several key interactions with the outer surface of FimH including π-π interactions with Tyr-48 and an H-bonding electrostatic interaction with the Arg-98/Glu-50 salt bridge. Dimeric analogues linked through the biaryl ring show an impressive 8-fold increase in potency relative to monomeric matched pairs and represent the most potent FimH antagonists identified to date. The FimH antagonists described herein hold great potential for development as novel therapeutics for the effective treatment of urinary tract infections.

Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety

A chiral rigid moiety which forms the basis of a new class of non-amphiphilic carbohydrate liquid crystals has been developed. This moiety contains a fully intact glucopyranose ring embedded in a trans-decalin structure. The original carbohydrate is substituted so that only two hydroxyl groups are left, resulting in derivatives with reduced hydrophilicity. The substituents R and X-R′ on the 4,6-O-ylidene β-D-glucopyranoside are in the equatorial position and can be varied extensively, using straightforward synthetic procedures. Investigations as to the requirements for R and X-R′ for inducing liquid-crystalline behavior have shown that at least one of the substituents should contain a large, polarizable aromatic moiety. An aromatic Schiff base fulfils this requirement.

Stannic chloride promoted synthesis of mannosides

Use of anhyd.SnCl4 has been described for the synthesis of aryl, arylalkyl and alkyl α-D-mannopyranosides.A possible mechanism for the formation of α-anomer in these reactions is discussed.