Síntese de naftoimidazóis derivados de β-lapachona com potenciais atividades biológicas

Abstract

The imidazole nucleus is present in the structures of many substances with pharmacological activities for different purposes. 6,6-Dimethyl-3,4,5,6-tetrahydrobenzo[7,8]-chromeno[5,6-d]imidazole (BLI-H) is a naftoimidazole obtained from β-lapachone - a naphthoquinone found in species of the bignoniaceae family, and which can also be obtained synthetically. The interest in studies with this naftoimidazole refers to synthetic possibilities for the imidazole ring of this molecule unsubstituted at positions 1,2 and 3, capable of undergoing nucleophilic substitution reactions with aliphatic and / or aromatic electrophiles. Furthermore, this which is the simplest naftoimidazole which can be obtained from β-lapachone, has shown antitripanosomal activity, although not as significant as some aryl-substituted β-lapachone derived naphthoimidazoles. This work reports the preparation of a series of compounds obtained by alkylation of BLI-H and the significant inhibitory activity on the growth of methicillin-resistant Staphylococcus aureus, Cryptococcus neoformans, Escherischia colii, Candida albicans, as well as Trypanosoma cruzi, achieved with these compounds. In addition to the products of alkylations, the search for derivatives with different substituents at carbon 2, led to the synthesis of two new β-lapachone-derived naphthoimidazoles with acyl, amine and bromine groups respectively, in that carbon