Biphenyl Gal and GalNAc FmlH Lectin Antagonists of Uropathogenic E. coli (UPEC): Optimization through Iterative Rational Drug Design

Journal of Medicinal Chemistry

Volumn 62, Issue 2, 2019, Pages 467-479

  Maddirala, Amarendar Reddy ^a   Klein, Roger ^a   Pinkner, Jerome S ^a   Kalas, Vasilios ^a   Hultgren, Scott J ^a   Janetka, James W ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY] 5 NITRO [1,1' BIPHENYL] 3 CARBOXYLIC ACID; 2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY] 6 METHOXY [1,1' BIPHENYL] 3 CARBOXYLIC ACID; 2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY] N METHYL [1,1' BIPHENYL] 3 CARBOXAMIDE; 2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY] N,N DIMETHYL [1,1' BIPHENYL] 3 CARBOXAMIDE; 5 NITRO [[3,4,5 TRIHYDROXY 6 (HYDROXYMETHYL) TETRAHYDRO 2H PYRAN 2 YL]OXY] [1,1' BIPHENYL] 3 CARBOXYLIC ACID; 6 [3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY] 3' (METHYLSULFONAMIDO) [1,1' BIPHENYL] 2 CARBOXYLIC ACID; ANTIBIOTIC AGENT; BIPHENYL GALACTOSAMINOSIDE DERIVATIVE; BIPHENYL GALACTOSIDE DERIVATIVE; CARBOXYLIC ACID; FIMH ADHESIN; LECTIN; METHYL [2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY][1,1' BIPHENYL] 3 YL]CARBAMATE; N [2 [[3' (CYCLOPROPANESULFONAMIDO) 6 METHYL [1,1' BIPHENYL] 2 YL) OXY] 4,5 DIHYDROXY 6 (HYDROXYMETHYL) TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; N [2 [[3,4,5 TRIHYDROXY 6 (HYDROXYMETHYL) TETRAHYDRO 2H PYRAN 2 YL]OXY] [1,1' BIPHENYL] 3 YL] METHANESULFONAMIDE; N [2 [[6 CYANO 3' (METHYLSULFONAMIDO) [1,1' BIPHENY] 2 YL]OXY] 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 3YL]ACETAMIDE; N [2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY][1,1' BIPHENYL] 3 YL] 2,2,2 TRIFLUOROACETAMIDE; N [2' [[3 ACETAMIDO 4,5 DIHYDROXY 6 (HYDROXYMETHYL)TETRAHYDRO 2H PYRAN 2 YL]OXY][1,1' BIPHENYL] 3 YL]ACETAMIDE; N [4,5 DIHYDROXY 6 (6 HDYROXYMETHYL) 2 [[3' (METHYLSULFONAMIDO) 6 (TRIFLUOROMETHYL) (1,1' BIPHENYL) 2 YL]OXY] TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; N [4,5 DIHYDROXY 6 (HYDROXYETHYL) 2 [[1 [3 (METHYLSULFONAMIDO)PHENYL]NAPHTHALEN 2 YL]OXY]TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; N [4,5 DIHYDROXY 6 (HYDROXYMETHYL) 2 [[3' (METHYLSULFONAMIDO) 6 NITRO [1,1' BIPHENYL] 2 YL]OXY]TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; N [4,5 DIHYDROXY 6 (HYDROXYMETHYL) 2 [[3' [(TRIFLUOROMETHYL)SULFONAMIDO] [1,1' BIPHENYL] 2 YL]OXY]TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; N [[4,5 DIHYDROXY 6 (HYDROXYMETHYL) 2 [[3' (METHYLSULFONAMIDO) [1,1' BIPHENYL] 2 YL]OXY]TETRAHYDRO 2H PYRAN 3 YL]ACETAMIDE; PROTEIN INHIBITOR; SULFONAMIDE; UNCLASSIFIED DRUG; ADHESIN; BIPHENYL; BIPHENYL DERIVATIVE; FMLH PROTEIN, E COLI; GALACTOSAMINE; GALACTOSE;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG DESIGN; DRUG HALF LIFE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ESCHERICHIA COLI INFECTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; IC50; LIGAND BINDING; LIVER MICROSOME; METABOLIC STABILITY; MOUSE; NONHUMAN; PHARMACOKINETIC PARAMETERS; RENAL CLEARANCE; URINARY TRACT INFECTION; UROPATHOGENIC ESCHERICHIA COLI; ANIMAL; CHEMISTRY; HALF LIFE TIME; HUMAN; METABOLISM; ORAL DRUG ADMINISTRATION; RAT; STRUCTURE ACTIVITY RELATION;

ADHESINS, ESCHERICHIA COLI; ADMINISTRATION, ORAL; ANIMALS; BIPHENYL COMPOUNDS; DRUG DESIGN; GALACTOSAMINE; GALACTOSE; HALF-LIFE; HUMANS; MICE; MICROSOMES, LIVER; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; URINARY TRACT INFECTIONS; UROPATHOGENIC ESCHERICHIA COLI;

EID: 85060526011     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.8b01561     Document Type: Article

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