title: 1,3-Azoles from ortho-naphthoquinones: synthesis of aryl substituted imidazoles and oxazoles and their potent activity against Mycobacterium tuberculosis.
abstract: Twenty-three naphthoimidazoles and six naphthoxazoles were synthesised and evaluated against susceptible and rifampicin- and isoniazid-resistant strains of Mycobacterium tuberculosis. Among all the compounds evaluated, fourteen presented MIC values in the range of 0.78 to 6.25 μg/mL against susceptible and resistant strains of M. tuberculosis. Five structures were solved by X-ray crystallographic analysis. These substances are promising antimycobacterial prototypes.
authors.affiliation: Núcleo de Pesquisas de Produtos Naturais, UFRJ, 21944-971 Rio de Janeiro, RJ, Brazil.
authors.forename: Kelly C G
authors.initials: KC
authors.lastname: Moura
authors.forename: Paula F
authors.initials: PF
authors.lastname: Carneiro
authors.forename: Maria do Carmo F R
authors.initials: Mdo C
authors.lastname: Pinto
authors.forename: José A
authors.initials: JA
authors.lastname: da Silva
authors.forename: Valéria R S
authors.initials: VR
authors.lastname: Malta
authors.forename: Carlos A
authors.initials: CA
authors.lastname: de Simone
authors.forename: Gleiston G
authors.initials: GG
authors.lastname: Dias
authors.forename: Guilherme A M
authors.initials: GA
authors.lastname: Jardim
authors.forename: Jéssica
authors.initials: J
authors.lastname: Cantos
authors.forename: Tatiane S
authors.initials: TS
authors.lastname: Coelho
authors.forename: Pedro E Almeida
authors.initials: PE
authors.lastname: da Silva
authors.forename: Eufrânio N
authors.initials: EN
authors.lastname: da Silva
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001393:Azoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007963:Leukocytes, Mononuclear / Q000166:cytology / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000995:Antitubercular Agents; D001393:Azoles; D007093:Imidazoles; D009285:Naphthoquinones; D010080:Oxazoles