title: Design and synthesis of new N-(5-trifluoromethyl)-1H-1,2,4-triazol-3-yl benzenesulfonamides as possible antimalarial prototypes.
abstract: A rational approach was used to synthesize a new set of 15 1H-1,2,4-triazol-3-yl benzenesulfonamide derivatives with the aim of developing new antimalarial lead compounds. These derivatives were prepared in yields between 50% and 62%, and their structures were elucidated using IR, ¹H-, ¹³C-, ¹⁹F-NMR, MS and elemental analysis. A docking study based on sulfonamides previously used against malaria identified trifluoromethyl-substituted derivatives to be the best lead compounds for new antimalarial drug development.
authors.affiliation: Departamento de Sintese Organica, Instituto de Tecnologia em Farmacos, Fundacao Oswaldo Cruz, Manguinhos, CEP 21041-250, Rio de Janeiro, RJ, Brazil. boechat@far.fiocruz.br
authors.forename: Nubia
authors.initials: N
authors.lastname: Boechat
authors.forename: Luiz C S
authors.initials: LC
authors.lastname: Pinheiro
authors.forename: Osvaldo A
authors.initials: OA
authors.lastname: Santos-Filho
authors.forename: Isabor C
authors.initials: IC
authors.lastname: Silva
mesh_terms: D000595:Amino Acid Sequence; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D020134:Catalytic Domain; D003198:Computer Simulation; D017124:Conserved Sequence; D003500:Cyclization; D004094:Dihydropteroate Synthase / Q000737:chemistry; D015195:Drug Design; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010963:Plasmodium falciparum / Q000201:enzymology; D011485:Protein Binding; D013411:Sulfadiazine / Q000737:chemistry; D013413:Sulfadoxine / Q000737:chemistry; D013415:Sulfalene / Q000737:chemistry; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D000096926:Benzenesulfonamides
chemical_list: D000962:Antimalarials; D004094:Dihydropteroate Synthase; D017611:Fluorine Compounds; D013411:Sulfadiazine; D013413:Sulfadoxine; D013415:Sulfalene; D013449:Sulfonamides; D014230:Triazoles; D000096926:Benzenesulfonamides