1295649-89-6

Upstream product

• 28619-28-5 4-bromophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 73183-34-3 bis(pinacol)diborane 
• 22860-22-6 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 287967-74-2 (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(4-iodophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 1312312-95-0 methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate 
• 1373346-95-2 4-(isoquinolin-5-yl)phenyl α-D-mannopyranoside 
• 1295649-66-9 methyl 5-[4-(α-D-mannopyranosyloxy)phenyl]thiophene-2-carboxylate 
• 1373346-93-0 4-(isoquinolin-7-yl)phenyl α-D-mannopyranoside 
• 1295649-64-7 methyl 5-[4-(α-D-mannopyranosyloxy)phenyl]pyridine-3-carboxylate 
• 1373346-92-9 1-{5-[4-(α-D-mannopyranosyloxy)phenyl]thiophen-3-yl}urea 
• 1295649-63-6 methyl 3-(carbamoylamino)-5-[4-(α-D-mannopyranosyloxy)phenyl]thiophene-2-carboxylate 
• 1295649-65-8 methyl 4-[4-(α-D-mannopyranosyloxy)phenyl]pyridine-2-carboxylate 
• 1373346-94-1 4-(quinazolin-6-yl)phenyl α-D-mannopyranoside 
• 1295649-67-0 methyl 5-[4-(α-D-mannopyranosyloxy)phenyl]thiophene-3-carboxylate 
• 1373346-96-3 4-(1-oxo-1,2-dihydroisoquinolin-7-yl)phenyl α-D-mannopyranoside 

Relevant academic research and scientific papers

MANNOSIDE COMPOUNDS AND METHODS OF USE THEREOF

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

Lead optimization studies on FimH antagonists: Discovery of potent and orally bioavailable ortho-substituted biphenyl mannosides

Herein, we describe the X-ray structure-based design and optimization of biaryl mannoside FimH inhibitors. Diverse modifications to the biaryl ring to improve druglike physical and pharmacokinetic properties of mannosides were assessed for FimH binding affinity based on their effects on hemagglutination and biofilm formation along with direct FimH binding assays. Substitution on the mannoside phenyl ring ortho to the glycosidic bond results in large potency enhancements several-fold higher than those of corresponding unsubstituted matched pairs and can be rationalized from increased hydrophobic interactions with the FimH hydrophobic ridge (Ile13) or "tyrosine gate" (Tyr137 and Tyr48) also lined by Ile52. The lead mannosides have increased metabolic stability and oral bioavailability as determined from in vitro PAMPA predictive model of cellular permeability and in vivo pharmacokinetic studies in mice, thereby representing advanced preclinical candidates with promising potential as novel therapeutics for the clinical treatment and prevention of recurring urinary tract infections.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

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

MANNOSE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION

Compounds of the formula (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are hydrogen or a substituent as described in the specification, are useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.