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Post-Functionalization of small Ply-functionalized molecules: a robust approach to the synthesis of new structural patterns with potential biological activity

Grant number: 18/02611-0
Support type:Regular Research Grants
Duration: May 01, 2018 - April 30, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Fernando Antonio Santos Coelho
Grantee:Fernando Antonio Santos Coelho
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
Assoc. researchers:Adriano Defini Andricopulo ; Nilton Soares Camilo ; Wanda Pereira Almeida

Abstract

This research project intends to continue the development of a line of research that explores the Morita-Baylis-Hillman (MBH) reaction, which is an organocatalysed process of formation of a new C-C Ã bond, leading to the synthesis of small poly-functionalized, which can be used as substrate for other chemical transformations. The research proposal was divided into two main projects and each of them divided into subprojects. In the first project, we intend to explore the general aspects of this reaction by initially testing its behavior in the presence of Bronsted acids. Although the usual catalysts of the Morita-Baylis-Hillman reaction may give rise to a very rapid acid-base reaction, preliminary results show a considerable increase in both the reaction rate and the yields, especially with aromatic aldehydes substituted with electrons donating groups, which behave very badly in this reaction. We also intend to explore novel bi-functional Lewis bases as catalysts for an asymmetric version of an MBH reaction between isatin and cycloenones. In the second project we intend to explore the use of adducts as substrates for the synthesis of pyrido-indolones, poly-functionalized dienes, macrolactones and macrolactams using novel synthetic approaches. The products obtained in this part of the proposal will be evaluated against triple negative human breast cancer cells. They will also be evaluated as inhibitors of acetylcholinesterase and against the parasites that cause malaria and leishmaniasis. (AU)

Scientific publications
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
SILVA, THIAGO S.; RODRIGUES, JR., MANOEL T.; SANTOS, HUGO; ZEOLY, LUCAS A.; ALMEIDA, WANDA P.; BARCELOS, ROSIMEIRE C.; GOMES, RALPH C.; FERNANDES, FABIO S.; COELHO, FERNANDO. Recent advances in indoline synthesis. Tetrahedron, v. 75, n. 14, p. 2063-2097, APR 5 2019. Web of Science Citations: 2.
FERNANDES, FABIO S.; RODRIGUES, JR., MANOEL T.; ZEOLY, LUCAS A.; CONTI, CAROLINE; ANGOLINI, CELIO F. F.; EBERLIN, MARCOS NOGUEIRA; COELHO, FERNANDO. Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in Morita-Baylis-Hillman Reactions. Journal of Organic Chemistry, v. 83, n. 24, p. 15118-15127, DEC 21 2018. Web of Science Citations: 1.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.