Methodology for Monobactam Diversification: Syntheses and Studies of 4-Thiomethyl Substituted β-Lactams with Activity against Gram-Negative Bacteria, Including Carbapenemase Producing Acinetobacter baumannii

Journal of Medicinal Chemistry

Volumn 60, Issue 21, 2017, Pages 8933-8944

  Carosso, Serena ^a   Liu, Rui ^a   Miller, Patricia A ^a   Hecker, Scott J ^b   Glinka, Tomasz ^b   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b Medicines Company   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(9H FLUOREN 9YL)METHYL [2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETIDIN 3 YL]CARBAMATE; 1 (ALLYLOXY) 4 (BROMOMETHYL)AZETIDIN 2 ONE; 1 (ALLYLOXY) 4 [(CYCLOHEXYLTHIO)METHYL]AZETIDIN 2 ONE; 1 (ALLYLOXY) 4 [(TRITYLTHIO)METHYL]AZETIDIN 2 ONE; 1 (ALLYLOXY) 4 [[(4,5 DIHYDROTHIAZOL 2 YL)THIO]METHYL]AZETIDIN 2 ONE; 1 ALLYLOXY 4 OXOAZETIDIN 2 YLMETHYL ETHANETHIOATE; 2 [[(2 METHOXY 2 OXOETHYL)THIO]METHYL] 4 OXO 3 (2 PHENYLACETAMIDO)AZETIDINE 1 SULFONATE; 2 [[[1 (2 AMINOTHIAZOL 5 YL] 2 [[2 [8 (2,3 DIHYDROXYBENZOYL) 14 (2,3 DIHYDROXYPHENYL) 6,14 DIOXO 2 THIA 5,8,13 TRIAZATETRADECYL] 4 OXO 1 SULFOAZETIDIN 3 YL]AMINO] 2 OXOETHYLIDENE]AMINO]OXY] 2 METHYLPROPANOIC ACID; 2,5 DIOXOPYRROLIDIN 1 YL 2 (2 AMINOTHIAZOL 5 YL) 2 (METHOXYIMINO)ACETATE; 3 [2 (2 AMINOTHIAZOL 5 YL) 2 [[(2 CARBOXYPROPAN 2 YL)OXY]IMINO]ACETAMIDO] 2 [[(2 AMMONIOETHYL)THIO]METHYL] 4 OXOAZETIDINE 1 SULFONATE POTASSIUM SALT; 3 [2 (2 AMINOTHIAZOL 5 YL) 2 [[[1 (TERT BUTOXY) 2 METHYL 1 OXOPROPAN 2 YL]OXY]IMINO]ACETAMIDO] 2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETDINE 1 SULFONATE; 3 [2 (2 AMINOTHIAZOL 5 YL] 2 (METHOXYIMINO)ACETAMIDO] 2 [[(2 AMMONIOETHYL)THIO]METHYL] 4 OXOAZETIDINE 1 SULFONATE POTASSIUM SALT; 3 [2 (2 AMINOTHIAZOL 5 YL] 2 (METHOXYIMINO)ACETAMIDO] 2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETIDINE 1 SULFONATE; 3[[[(9H FLUOREN 9 YL)METHOXY]CARBONYL]AMINO] 2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETIDINE 1 SULFONATE; BETA LACTAM DERIVATIVE; CATECHOL; METHYL 2 [[(3 AZIDO 4 OXOAZETIDIN 2 YL)METHYL]THIO]ACETATE; METHYL 2 [[[1 (ALLYLOXY) 4 OXOAZETIDIN 2 YL]METHYL]THIO]ACETATE; METHYL 2 [[[4 OXO 3 (2 PHENYLACETAMIDO)AZETIDIN 2 YL]METHYL]THIO]ACETATE; MONOBACTAM DERIVATIVE; POTASSIUM 2 [[(2 METHOXY 2 OXOETHYL)THIO]METHYL] 4 OXO 3 (2 PHENYLACETAMIDO)AZETIDINE 1 SULFONATE; POTASSIUM 3 [2 (2 AMINOTHIAZOL 5 YL) 2 [[[1 (TERT BUTOXY) 2 METHYL 1 OXOPROPAN 2 YL]OXY]IMINO]ACETAMIDO] 2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETDINE 1 SULFONATE; POTASSIUM 3 [2 (2 AMINOTHIAZOL 5 YL] 2 (METHOXYIMINO)ACETAMIDO] 2 [[[2 [(TERT BUTOXYCARBONYL)AMINO]ETHYL]THIO]METHYL] 4 OXOAZETIDINE 1 SULFONATE; TERT BUTYL 2 [[(1 (2 AMINOTHIAZOL 5 YL) 2 [(2,5 DIOXOPYRROLIDIN 1 YL)OXYETHYLIDENE]AMINO]OXY] 2 METHYLPROPANOATE; TERT BUTYL [2 [[(3 AZIDO 4 OXOAZETIDIN 2 YL)METHYL]THIO]ETHYL]CARBAMATE; TERT BUTYL [2 [[[1 (ALLYLOXY) 4 OXOAZETIDIN 2 YL]METHYL]THIO]ETHYL]CARBAMATE; TERT BUTYL [2 [[[3 [2 (2 AMINOTHIAZOL 5 YL) 2 (METHOXYIMINO)ACETAMIDO] 4 OXOAZETIDIN 2 YL]METHYL]THIO]ETHYL]CARBAMATE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; BETA LACTAM; BETA LACTAMASE; CARBAPENEMASE; CATECHOL DERIVATIVE;

ACINETOBACTER BAUMANNII; ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; METHODOLOGY; NONHUMAN; STRUCTURE ACTIVITY RELATION; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; MICROBIAL SENSITIVITY TEST; PROCEDURES; SYNTHESIS;

ACINETOBACTER BAUMANNII; BACTERIAL PROTEINS; BETA-LACTAMASES; BETA-LACTAMS; CATECHOLS; GRAM-NEGATIVE BACTERIA; METHODS; MICROBIAL SENSITIVITY TESTS; MONOBACTAMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 85033385340     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.7b01164     Document Type: Article

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