Directed functionalization of quinoxalines aiming the synthesis of bioactive compounds

• Grant number: 12/08589-0
• Support type: Scholarships in Brazil - Doctorate
• Effective date (Start): July 01, 2012
• Effective date (End): February 29, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal researcher: Giuliano Cesar Clososki
• Grantee: Samuel Remotto Alves Ferreira
• Home Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
• Associated research grant: 08/04762-4 - New synthetic methods for the preparation of bioactive compounds, AP.JP

Abstract

Quinoxalines are heterocyclic compounds that have pyrazine and benzene rings in its structures. In addition of the applications as dye and new materials, the quinoxalines are remarkable for their enormous potential of applications in medicinal chemistry, where has already demonstrated antiviral, anti-inflammatory, antimalarial, antidepressant, antitumor and others activities. Although the importance of this class of substances, there are few studies about the direct functionalization of quinoxalines using organometallic bases. Thus, the main objective of this project is to develop a methodology that allows direct metallation of quinoxalines substituted with functional groups using new bases of zinc derived from TMPH. The reaction of the organometallic intermediates with different electrophiles could lead to the preparation of highly functionalized quinoxalines.In order to demonstrate the synthetic importance of the developed methodologies, we plan to apply these in the synthesis or structural modification of bioactive quinoxalines. Furthermore, the quinoxalines which will be synthesized in this project, especially those that present new structures, may have their biological activities evaluated by scientific groups which work with biological activity of natural and synthetics compounds at the of Faculty Pharmaceutical Sciences of Ribeirão Preto - USP.The proposals presented here are part of the project "Development of New Synthetic Methods Aiming at Preparation of Bioactive Molecules", approved by FAPESP through the Young Researcher Program with the objective of to centralize research groups that work with modern themes and with international insertion.

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)

FERREIRA, SAMUEL R. A.; FRANCO, MARCIA S. F.; DINIZ, EVELYN M. L. P.; EMERY, FLAVIO DA SILVA; CLOSOSKI, GIULIANO CESAR. Drug Likeness and Selective Functionalization of Quinoxalines. CURRENT ORGANIC SYNTHESIS, v. 12, n. 6, p. 714-729, 2015. Web of Science Citations: 5.

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

FERREIRA, Samuel Remotto Alves. Directed functionalization of quinoxalines aiming the synthesis of bioactive compounds. 2016. Doctoral Thesis - Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto Ribeirão Preto.