title: Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.
abstract: New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.
authors.affiliation: Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, Brazil. hberaldo@ufmg.br.
authors.forename: Débora C
authors.initials: DC
authors.lastname: Reis
authors.forename: Angel A Recio
authors.initials: AA
authors.lastname: Despaigne
authors.forename: Jeferson G
authors.initials: JG
authors.lastname: Da Silva
authors.forename: Nayane F
authors.initials: NF
authors.lastname: Silva
authors.forename: Camila F
authors.initials: CF
authors.lastname: Vilela
authors.forename: Isolda C
authors.initials: IC
authors.lastname: Mendes
authors.forename: Jacqueline A
authors.initials: JA
authors.lastname: Takahashi
authors.forename: Heloisa
authors.initials: H
authors.lastname: Beraldo
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002963:Cladosporium / Q000187:drug effects; D018556:Crops, Agricultural; D006835:Hydrazones / Q000737:chemistry / Q000494:pharmacology*; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D009761:Nystatin / Q000494:pharmacology; D010935:Plant Diseases / Q000382:microbiology; D013882:Thiosemicarbazones / Q000737:chemistry / Q000494:pharmacology*; D014961:X-Ray Diffraction
chemical_list: D000935:Antifungal Agents; D006835:Hydrazones; D007093:Imidazoles; D013882:Thiosemicarbazones; D009761:Nystatin