title: Synthesis, characterization, solvatochromism and biological properties of 2,2'-((1E,1'E)-((1,2,5-oxadiazole-3,4-diyl)bis (azanylylidene))bis(methan-ylylidene))bis(4-(phenyldiazenyl)phenol).
abstract: Azo-azomethine dyes 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyl diazenyl)phenols (2a-h) have been synthesized by condensation reaction of 3,4-diamino-1,2,5-oxadiazole with 2-hydroxy-5-[(E)-(aryldiazenyl)]benzaldehyde (1a-h) in methanol. The structures of dyes have been characterized by elemental analysis, mass, IR, UV-Vis, 1H and 13С NMR spectroscopy. UV-Vis absorption spectra indicated enol-keto tautomeric and positive solvatochromism in compounds 2a-h which is dependent on the substitution, solvent, pH and environment temperature. The synthesized compounds were investigated for their in vitro antioxidant activity by diphenylpicrylhydrazyl assay. Compounds substituted with electron donating groups, such as, alkyl and methoxy groups showed moderate antioxidant activity. The in vitro antibacterial activity of all compounds was determined by disk diffusion method. The test compounds showed varying degree of inhibition against B. cereus and S. aureus strains.
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran. Electronic address: alikakanejadifard@yahoo.com.
authors.forename: Ali
authors.initials: A
authors.lastname: Kakanejadifard
authors.affiliation: Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Farideh
authors.initials: F
authors.lastname: Azarbani
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Zeinab
authors.initials: Z
authors.lastname: Saki
authors.affiliation: Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Sahar
authors.initials: S
authors.lastname: Kakanejadifard
authors.affiliation: Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
authors.forename: Abedin
authors.initials: A
authors.lastname: Zabardasti
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004126:Dimethylformamide / Q000737:chemistry; D004583:Electrons; D005663:Furans / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019800:Phenol / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013696:Temperature
chemical_list: C000595799:2,2'-((1E,1'E)-((1,2,5-oxadiazole-3,4-diyl)bis(azanylylidene))bis(methan-ylylidene))bis(4-(phenyldiazenyl)phenol; D000900:Anti-Bacterial Agents; D005663:Furans; D010069:Oxadiazoles; D010636:Phenols; D012997:Solvents; D019800:Phenol; C018674:tetrahydrofuran; D004126:Dimethylformamide; D004121:Dimethyl Sulfoxide
keywords: Antibacterial activity; Antioxidant activity; Azo-dyes; Azo–azomethine; Schiff base; Solvatochromism