Enantioselective synthesis and anti-parasitic properties of aporphine natural products

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art_PIEPER_Enantioselective_synthesis_and_antiparasitic_properties_of_aporphine_natural_2020.PDF.pdf (581.61 KB)
Citações na Scopus
21
Tipo de produção
article
Data de publicação
2020
DOI
Scopus
Web of Science
Título da Revista
ISSN da Revista
Título do Volume
Editora
PERGAMON-ELSEVIER SCIENCE LTD
Autores
PIEPER, Pauline
MCHUGH, Eliza
TEMPONE, Andre G.
ANDERSON, Edward A.
Citação
TETRAHEDRON, v.76, n.2, Special Issue, article ID 130814, 8p, 2020
Projetos de Pesquisa
Unidades Organizacionais
Fascículo
Resumo
Chagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.
Palavras-chave
Natural products, Aporphine, Leishmania infantum, Trypanosoma cruzi, Alkaloid, Palladium catalyzed arylation
URI
https://observatorio.fm.usp.br/handle/OPI/35727
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Coleções
Artigos e Materiais de Revistas Científicas - IMT