Organocatalytic asymmetric vinylogous 1,4-addition of alpha,alpha-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity

Autor(es)

Martelli, Lorena S. R. ^[1] ; Vieira, Lucas C. C. ^{[1, 2]} ; Paixao, Marcio W. ^[1] ; Zukerman-Schpector, Julio ^[1] ; de Souza, Juliana O. ^[3] ; Aguiar, Anna Caroline C. ^[3] ; Oliva, Glaucius ^[3] ; Guido, Rafael V. C. ^[3] ; Correa, Arlene G. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Fed Mato Grosso, Inst Engn, BR-78060900 Cuiaba, MT - Brazil

^[3] Univ Sao Paulo, Ctr Innovat Biodivers & Drug Discovery, Sao Carlos Inst Phys, BR-13563120 Sao Carlos, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron; v. 75, n. 25, p. 3530-3542, JUN 21 2019.
• Citações Web of Science: 1

Resumo

The organocatalysed asymmetric vinylogous Michael addition of alpha,alpha-dicyanoolefins to alpha,beta-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of alpha,alpha-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity. (C) 2019 Elsevier Ltd. All rights reserved. (AU)

• Processo FAPESP: 17/26679-0 - Derivados 4-quinolinonas como candidatos a fármacos antimaláricos: caracterização da atividade Antiplasmodial in vitro, in vivo e de modo de ação
• Beneficiário: Juliana Oliveira de Souza
• Modalidade de apoio: Bolsas no Brasil - Mestrado
• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs