Acta Scientiarum: Technology (Jul 2005)
Synthesis, toxicity towards brine shrimp (Artemia salina Leach) and antimicrobial activity evaluation of 3,5-diphenylchlorinated-1,2,4- oxadiazoles = Síntese, toxicidade frente a Artemia salina Leach e avaliação da atividade antimicrobiana de 1,2,4-oxadiazóis-3,5-difenilclorados
Abstract
The known oxadiazoles 3,5-bis-(phenyl)-1,2,4-oxadiazole (3a); the 3-(4-chlorophenyl)-5-phenyl-1,2,4-oxadiazole (3b); and the new 3,5-diphenylchlorinated-1,2,4-oxadiazoles 3c-e were synthesized from the reaction of benzamidoximes with an appropriated acid chloride and cyclisation of the resulting O-acylbenzamidoxime intermediate. The compounds synthesized were characterized on the basis of their IR, NMR (1D and 2D) and mass spectral data. Compounds 3a-e were evaluated for their antimicrobial activity and for their toxicity towards brineshrimp (Artemia salina Leach). Os oxadiazóis 3,5-bis-(fenil)-1,2,4- oxadiazol (3a) e 3-(4-clorofenil)-5-fenil-1,2,4-oxadiazol (3b), já descritos na literatura, e, os 1,2,4- oxadiazóis-3,5-fenilclorados inéditos 3c-e, foram sintetizados pela reação de bezamidoximas com um cloreto de ácido apropriado, seguido da ciclização do intermediário O-acilíco resultante. Os compostos obtidos foram caracterizados com base nas análises dos dados espectroscópicos de IV, EM e RMN (uni- e bidimensionais). Os compostos 3a-e foram submetidos a bioensaios paraavaliação de atividade antimicrobiana e, de toxicidade frente ao microcrustáceo Artemia salina Leach.
