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Doctoral Thesis
DOI
https://doi.org/10.11606/T.59.2002.tde-16052024-111710
Document
Author
Full name
Marcia Maisa de Freitas Afonso
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
Ribeirão Preto, 2002
Supervisor
Committee
Federman Neto, Alberto (President)
Albuquerque, Sérgio de
Batista, Alzir Azevedo
Marzorati, Liliana
Oliveira, Dioneia Camilo Rodrigues de
Title in Portuguese
Estudo da condensação Claisen-Schmidt aplicada à compostos organometálicos e atividade tripanocida de novas chalconas metaladas com elementos de transição
Keywords in Portuguese
Chalconas organometálicas
Compostos organometálicos
Tripanomicidas
Abstract in Portuguese
A Condensação Claisen-Schmidt (condensação aldólica seguida de desidratação espontânea) foi estudada para ser aplicada a substratos (aldeídos e cetonas) organometálicos de caráter aromático. Um protocolo simples para a reação foi desenvolvido, substituindo o catalisador clássico da Claisen-Schmidt orgânica (hidróxido de sódio) por hidróxido de potássio. A reação permite alta funcionalização dos substratos organometalados, formando cetonas alfa-beta insaturadas contendo pelo menos uma das unidades aromáticas. Essas cetonas são chamadas de chalconas. Como outras chalconas orgânicas de origem natural ou sintéticas, as chalconas organometálicas obtidas demonstraram possuir de moderado a muito alto grau de atividade tripanomicida, portanto potencialmente anti-chagásica, medida através da inibição da enzima gliceraldeído-3-fosfato desidrogenase de Trypanossoma cruzi. Foram preparadas e testadas, uma chalcona organometálica conhecida e vários outros compostos novos. Uma nova nomenclatura simplificada foi proposta para chalconas organometálicas.
Title in English
Study of Claisen-Schmidt condensation applied to organometallic compounds and trypanocidal activity of new chalcones metallated with transition elements
Keywords in English
Organometallic chalcones
Organometallic compounds
Trypanomicides
Abstract in English
The Claisen-Schmidt reaction (aldol condensation with expontaneous splitting of water) was studied and aplied to organometallic aromatic substrates (aldehydes and ketones). A simplified protocol for the reaction was developed, substituting the sodium hydroxide (the classical catalyst) by potassium hydroxide. The reaction is a manner to introduce high functionalization into organometallic aromatic substrates, fonning alpha, beta insaturated ketones in witch at least one of the moities is aromatic. These kind of ketone is called chalcone. As well as other natural ar synthetic organic chalcones, the organometallic chalcones that were obtained, have moderate to high degree of tripanocidal activity against Trypanossoma cruzi, and therefore may be used as potencial new antichagasic drugs.
 
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001294571.pdf (9.05 Mbytes)
Publishing Date
2024-05-16
 
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