title: Synthesis and biological evaluation of 1,2,5-oxadiazole N-oxide derivatives as potential hypoxic cytotoxins and DNA-binders.
abstract: Several new 1,2,5-oxadiazole N-oxide derivatives were synthesized to be tested both as potential selective hypoxic cell cytotoxins and as DNA-binding agents. The compounds prepared included bis(1,2,5-oxadiazole N-oxide) derivatives and oxadiazole rings linked to naphthyl residues. The compounds were tested for their cytotoxicity in oxia and hypoxia and they proved to be non-selective and less active than the parent compounds 3-formyl-4-phenyl-1,2,5-oxadiazole N2-oxide (3) and 3-chloromethyl-4-phenyl-1,2,5-oxadiazole N2-oxide (4). The DNA-affinity assays showed that the compounds tested have poor affinity for this biomolecule.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de la República, Gral. Flores 2124, 11800 Montevideo, Uruguay.
authors.forename: H
authors.initials: H
authors.lastname: Cerecetto
authors.forename: M
authors.initials: M
authors.lastname: González
authors.forename: M
authors.initials: M
authors.lastname: Risso
authors.forename: G
authors.initials: G
authors.lastname: Seoane
authors.forename: A
authors.initials: A
authors.lastname: López de Ceráin
authors.forename: O
authors.initials: O
authors.lastname: Ezpeleta
authors.forename: A
authors.initials: A
authors.lastname: Monge
authors.forename: L
authors.initials: L
authors.lastname: Suescun
authors.forename: A
authors.initials: A
authors.lastname: Mombrú
authors.forename: A M
authors.initials: AM
authors.lastname: Bruno
mesh_terms: D000332:Aerobiosis; D000818:Animals; D015687:Cell Hypoxia / Q000187:drug effects / Q000502:physiology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects*; D002999:Clone Cells; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D003603:Cytotoxins; D010069:Oxadiazoles; D010087:Oxides; D004247:DNA