title: 5-benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials.
abstract: Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds.
authors.affiliation: Department of Chemistry, The University of Adelaide, Adelaide, South Australia 5005, Australia.
authors.forename: Ondrej
authors.initials: O
authors.lastname: Zvarec
authors.forename: Steven W
authors.initials: SW
authors.lastname: Polyak
authors.forename: William
authors.initials: W
authors.lastname: Tieu
authors.forename: Kevin
authors.initials: K
authors.lastname: Kuan
authors.forename: Huanqin
authors.initials: H
authors.lastname: Dai
authors.forename: Daniel Sejer
authors.initials: DS
authors.lastname: Pedersen
authors.forename: Renato
authors.initials: R
authors.lastname: Morona
authors.forename: Lixin
authors.initials: L
authors.lastname: Zhang
authors.forename: Grant W
authors.initials: GW
authors.lastname: Booker
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001597:Benzylidene Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012236:Rhodanine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D001597:Benzylidene Compounds; D045162:Thiazolidinediones; D012236:Rhodanine; C089946:2,4-thiazolidinedione