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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 9
[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
Total Affiliations: 3
Document type: Journal article
Source: Tetrahedron; v. 75, n. 25, p. 3530-3542, JUN 21 2019.
Web of Science Citations: 0

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)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support type: Research Grants - Research Centers in Engineering Program
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 17/26679-0 - 4-Quinolone derivatives as antimalarial drug candidates: Antiplasmodial activity characterization in vitro, in vivo and of the mode of action
Grantee:Juliana Oliveira de Souza
Support type: Scholarships in Brazil - Master