| Grant number: | 13/20094-0 |
| Support Opportunities: | Regular Research Grants |
| Start date: | March 01, 2014 |
| End date: | February 29, 2016 |
| Field of knowledge: | Physical Sciences and Mathematics - Chemistry - Organic Chemistry |
| Principal Investigator: | Antônio Eduardo Miller Crotti |
| Grantee: | Antônio Eduardo Miller Crotti |
| Host Institution: | Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil |
| City of the host institution: | Ribeirão Preto |
| Associated researchers: | Daniele da Silva Ferreira ; Edson Luiz Lopes Baldin ; Lizandra Guidi Magalhães ; Paulo Marcos Donate ; Renato Luis Tame Parreira ; Ricardo Vessecchi Lourenço ; Viviane Rodrigues Esperandim |
Abstract
Neglected tropical diseases are a group of diseases that affect poor areas in Africa, Asia and Latin America. These include schistosomiasis, leishmaniasis and Chagas disease that represent major public health problems in Brazil. In agriculture, the silverleaf whitefly (Bemisia tabaci biotype B) is one of the major pests in tomato crops. Studies have reported the anti-parasitic and insecticidal potential of various benzofuran derivatives, such as dihydrobenzofuran neolignans. Reactions between ortho-hydroxyaldehydes or ortho -hydroxy-ketones and ±-halogenated aldehydes or ketones are the most used synthetic methods for constructing the benzofuran system. In the case of the synthesis of dihydrobenzofuran neolignans, the oxidative coupling between phenylpropanoids units is the most widely used, and the regioselectivity of such coupling depends on the oxidizing agent employed. However, no detailed studies on the intermediates involved in these reactions were found in the literature nor systematic studies on the fragmentation pathways of these compounds in the gas phase using electrospray ionization tandem mass spectrometry (ESI-EM/EM). The goal of this project is the synthesis of some dihydrobenzofuran neolignans by oxidative coupling, as well as other benzofuran compounds employing various routes.. The obtained compounds will be evaluated for their schistosomicidal, leishmanicidal, trypanocidal and insecticidal activities. The mechanisms of the oxidative coupling of phenylpropanoid will be investigated by ESI-MS/MS. The ESI-MS/MS technique also will be used in combination with data obtained from Computational Chemistry for the elucidation of fragmentation pathways of dihydrobenzofuran neolignans and other benzofuran compounds, aiming to obtain structure-fragmentation correlations that could make enable the identification/dereplication of these compounds in complex mixtures in complex mixtures by ESI-MS/MS or HPLC-ESI-MS/MS. (AU)
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