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Previous issue date: 2009-09-25 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior, CAPES, Brasil. / This work is part of a research project which investigates the utilization of abundant
and accessible natural products in the synthesis of new molecules with potential activity
against Chagas? disease. Recent studies carried out in our laboratory showed activity
against Trypanosoma cruzi for piperine, a major component of Piper nigrum and for a
series of its derivatives and analogues. Using bioisosterism as a strategy for molecular
modification, we describe here the design, synthesis and antiparasitic evaluation of
class of derivatives of 1,2,4-oxadiazole. The key step of the synthetic strategy used
involved the SNAC reaction of the benzamidoxima with acid chlorides followed by
cyclization, which allowed the preparation of eight new 1,2,4-oxadiazole The evaluation
of the toxic activity of these new derivatives against epimastigote form of T. cruzi
confirmed the bioisosteric relationship between the natural amide and the new products
prepared, showing the oxadiazole 55 direct derived from piperine, as the most active
compound in the series. / Este trabalho se insere numa linha de pesquisa que visa a utiliza??o de produtos
naturais abundantes e access?veis na s?ntese de novas mol?culas com potencial atividade
anti-chag?sica. Estudos recentes em nosso laborat?rio demonstraram a atividade
antiparasit?ria da piperina e de uma s?rie de derivados e an?logos sobre o Trypanosoma
cruzi, agente etiol?gico da doen?a de Chagas. Utilizando o bioisosterismo como
estrat?gia de modifica??o molecular, descrevemos aqui o planejamento, a s?ntese e a
avalia??o antiparasit?ria de derivados da classe dos 1,2,4-oxadiaz?is. A etapa-chave da
estrat?gia sint?tica utilizada envolveu a rea??o de SNAC da benzamidoxima com cloretos
de ?cidos, seguida de cicliza??o, que permitiu a prepara??o de oito novos 1,2,4-
oxadiaz?is. A avalia??o da atividade t?xica destes novos derivados contra a forma
epimastigota do T. cruzi confirmou a rela??o bioisost?rica entre a amida natural e os
novos derivados preparados, evidenciando o oxadiazol 55 derivado direto da piperina,
como o composto mais ativo da s?rie.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:jspui/2003 |
| Date | 25 September 2009 |
| Creators | Soares, Breno Almeida |
| Contributors | Lima, Marco Edilson Freire de, Lima, Lidia Moreira, Ferreira, Aur?lio Baird Buarque, Pinheiro, S?rgio |
| 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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