New 5-benzylidenethiazolidin-4-one inhibitors of bacterial MurD ligase: Design, synthesis, crystal structures, and biological evaluation

European Journal of Medicinal Chemistry

Volumn 46, Issue 11, 2011, Pages 5512-5523

  Zidar, Nace ^a   Tomašić, Tihomir ^a   Šink, Roman ^a   Kovač, Andreja ^a   Patin, Delphine ^b   Blanot, Didier ^b   Contreras Martel, Carlos ^c,d   Dessen, Andréa ^c,d   Premru, Manica Müller ^a   Zega, Anamarija ^a   Gobec, Stanislav ^a   Mašič, Lucija Peterlin ^a   Kikelj, Danijel ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b INSTITUTE FOR INTEGRATIVE BIOLOGY OF THE CELL I2BC   (France)

^c INSTITUT DE BIOLOGIE STRUCTURALE   (France)

^d DIF   (France)

Author keywords

5 Benzylidenerhodanine; 5 Benzylidenethiazolidine 2,4 dione; Inhibitor; MurD ligase; Peptidoglycan biosynthesis

Indexed keywords

2 [3 [[4 [(2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL)METHYL]PHENOXY]METHYL]BENZAMIDO)PENTANEDIOIC ACID; 2 [4 [[2 (CARBOXYMETHOXY) 4 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]BENZAMIDO]PENTANEDIOIC ACID; 2 [4 [[3 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]BENZAMIDO]PENTANEDIOIC ACID; 2 [4 [[3 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]PHENYLSULFONAMIDO]PENTANEDIOIC ACID; 4 [(3 FORMYLPHENOXY)METHYL]BENZOIC ACID; 4 BENZYLOXY 3 HYDROXYBENZALDEHYDE; ANTIBIOTIC AGENT; DIMETHYL 2 [ 4 (BROMOMETHYL)PHENYLSULFONAMIDO]PENTANEDIOATE; DIMETHYL 2 [3 (CHLOROMETHYL)BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [3 [[4 (CHLOROMETHYL)PHENOXY]METHYL]BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [3 [[4 (HYDROXYMETHYL)PHENOXY]METHYL]BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [3 [[4 [(2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL)METHYL]PHENOXY]METHYL]BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [4 (CHLOROMETHYL)BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [4 [(3 FORMYLPHENOXY)METHYL]BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [4 [(3 FORMYLPHENOXY)METHYL]PHENYLSULFON AMIDO]PENTANEDIOATE; DIMETHYL 2 [4 [[2 (2 METHOXY 2 OXOETHOXY) 4 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]PHENOXY]METHYL]BENZAMIDO)PENTANEDIOATE; DIMETHYL 2 [4 [[3 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]BENZAMIDO]PENTANEDIOATE; DIMETHYL 2 [4 [[3 [(4 OXO 2 THIOXOTHIAZOLIDIN 5 YLIDENE)METHYL]PHENOXY]METHYL]PHENYLSULFONAMIDO]PENTANEDIOATE; DIMETHYL 2 [4 [[4 FORMYL 2 (2 METHOXY 2 OXOETHOXY)PHENOXY]METHYL]BENZAMIDO]PENTANEDIOATE; METHYL 2 (2 BENZYLOXY 5 FORMYLPHENOXY)ACETATE; METHYL 2 (5 FORMYL 2 HYDROXYPHENOXY)ACETATE; METHYL 4 [(3 FORMYLPHENOXY)METHYL]BENZOATE; N ACETYLMURAMOYLALANINE AMIDASE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG DESIGN; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ENZYME ACTIVE SITE; HYDROGEN BOND; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROCESS OPTIMIZATION; PSEUDOMONAS AERUGINOSA; RADIOACTIVITY; STAPHYLOCOCCUS AUREUS; X RAY CRYSTALLOGRAPHY;

AMIDES; BACTERIA; BENZYLIDENE COMPOUNDS; CHEMISTRY TECHNIQUES, SYNTHETIC; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDE SYNTHASES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINES; URACIL;

EID: 80054935500     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.09.017     Document Type: Article

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