title: Synthesis and microbiological evaluation of new 2- and 2,3-diphenoxysubstituted naphthalene-1,4-diones with 5-oxopyrrolidine moieties.
abstract: New 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives containing hydrazone, azole, diazole, oxadiazole fragments, as well as 2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinone derivatives were synthesized. The structure of all compounds has been confirmed by NMR, IR, mass spectra, and elemental analysis data. Methyl 1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarboxylate demonstrated potential antibacterial and antifungal activities as determined by diffusion and serial dilution methods, while N'-[(4-bromophenyl)methylidene]-1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarbohydrazide and 2-{3-[4-(1,2,3-oxadiazol-5-yl)-2-oxo-1-pyrrolidinyl]phenoxy}-3-{3-[4-(1,3,4-oxadiazol-2-yl)-2-oxo- 1-pyrrolidinyl]phenoxy}naphthoquinone showed antifungal activity against Candida tenuis and Aspergillus niger at low concentrations, as determined by the serial dilution method. The substitution of the methoxy fragment by N-containing substituents in monophenoxy substituted naphthoquinones was found to decrease their activity against Mycobacterium luteum. Besides, introduction of the second phenoxy substituted fragment increased the antifungal activity against Candida tenuis and Aspergillus niger at lower concentrations.
authors.affiliation: Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl 19, LT-50254 Kaunas, Lithuania. ilona.jonuskiene@ktu.lt
authors.forename: Aušra
authors.initials: A
authors.lastname: Voskienė
authors.forename: Birutė
authors.initials: B
authors.lastname: Sapijanskaitė
authors.forename: Vytautas
authors.initials: V
authors.lastname: Mickevičius
authors.forename: Ilona
authors.initials: I
authors.lastname: Jonuškienė
authors.forename: Maryna
authors.initials: M
authors.lastname: Stasevych
authors.forename: Olena
authors.initials: O
authors.lastname: Komarovska-Porokhnyavets
authors.forename: Rostyslav
authors.initials: R
authors.lastname: Musyanovych
authors.forename: Volodymyr
authors.initials: V
authors.lastname: Novikov
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D001234:Aspergillus niger / Q000187:drug effects / Q000254:growth & development; D002175:Candida / Q000187:drug effects / Q000254:growth & development; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects / Q000254:growth & development; D009281:Naphthalenes / Q000138:chemical synthesis*; D009285:Naphthoquinones / Q000138:chemical synthesis; D010069:Oxadiazoles / Q000138:chemical synthesis
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D009281:Naphthalenes; D009285:Naphthoquinones; D010069:Oxadiazoles; C031721:naphthalene; C035342:1,4-naphthoquinone