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Previous issue date: 2016-04-14 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior - CAPES / 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 ?-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 ?-lapachone, has shown antitripanosomal activity, although not as significant as some aryl-substituted ?-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 ?-lapachone-derived naphthoimidazoles with acyl, amine and bromine groups respectively, in that carbon / N?cleos imidaz?licos est?o presentes nas estruturas de muitas subst?ncias com atividades farmacol?gicas, para diferentes finalidades. O 6,6-dimetil-3,4,5,6-tetra-hidrobenzo-[7,8]cromeno[5,6-d]imidazol (BLI-H) ? um naftoimidazol obtido a partir da ?-lapachona ? uma naftoquinona encontrada em esp?cies da fam?lia das bignoni?ceas e que tamb?m pode ser obtida sinteticamente.1 O interesse nos estudos com este naftoimidazol se refere ?s possibilidades sint?ticas para o n?cleo imidaz?lico desta mol?cula, n?o substitu?do nas posi??es 1, 2 e 3, capaz de sofrer rea??es de substitui??es nucleof?lica alif?tica e/ou eletrof?lica arom?tica. Al?m disso, este, que ? o naftoimidazol mais simples que pode ser obtido a partir da ?-lapachona, j? demonstrou seu potencial na atividade antitripanoss?mica, embora n?o t?o expressiva quanto as de outros naftoimidaz?is, substitu?dos, derivados de ?-lapachona.
Este trabalho relata a prepara??o de uma s?rie de compostos obtidos por alquila??o de BLI-H e a atividade inibit?ria significativa destes compostos sobre o crescimento de Staphylococcus aureus resistente ? meticilina, Escherischia colii, Cryptococcus neoformans, Candida albicans, assim como Trypasoma cruzi.
Al?m dos produtos das N-alquila??es, a busca por derivados com diferentes substituintes no carbono 2, levou ? s?ntese de tr?s novos naftoimidaz?is com grupos acila, bromo e amina, respectivamente, neste carbono
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/1713 |
| Date | 14 April 2016 |
| Creators | Silva, Leonardo Araujo |
| Contributors | Ferreira, Aur?lio Baird Buarque, Silva, Ari Miranda da, Garden, Simon J., Suzart, Luciano Ramos, Silva, B?rbara Vasconcellos da, Santos, Cl?udio E. Rodrigues dos |
| Publisher | Universidade Federal Rural do Rio de Janeiro, Programa de P?s-Gradua??o em Qu?mica, UFRRJ, Brasil, Instituto de Ci?ncias Exatas |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFRRJ, instname:Universidade Federal Rural do Rio de Janeiro, instacron:UFRRJ |
| Rights | info:eu-repo/semantics/openAccess |
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