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Application of organometallic reagents in the functionalization of indolizines of synthetic interest

Grant number: 11/20742-6
Support Opportunities:Scholarships in Brazil - Doctorate
Effective date (Start): February 01, 2012
Effective date (End): January 31, 2015
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Giuliano Cesar Clososki
Grantee:Mônica Franco Zannini Junqueira Toledo
Host 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


Among the heterocycles containing a pyridine ring in their structure, the indolizines are very important because they are commonly found in the structure of substances of medicinal interest. Besides its application against tuberculosis and leishmaniasis, the biological activity of this class of compounds has allowed their use as analgesics, anti-inflammatory, antiviral and antitumor.Although the importance of this class of substances, data in the literature on the direct functionalization indolizines using organometallic bases are rare. Thus, the main objective of this project is to develop a methodology that allows direct functionalization of indolizines using lithium, magnesium and zinc amides. The reaction of the organometallic intermediates with different electrophiles should allow to prepare highly functionalized indolizines.In order to demonstrate the importance of the synthetic methodologies developed, we intend to apply these in the synthesis or structural modification of bioactive indolizines such as STA-5312. In addition, the indolizines that will be synthesized in this project could be tested by the groups of the Faculdade de Ciências Farmacêuticas de Ribeirão Preto - USP dedicated to the biological evaluation of natural and synthetic componds.The proposals presented here are part of the project "Development of New Synthetic Methods Aiming Preparation of Bioactive Molecules", approved by FAPESP through the Young Researcher Program with the objective to give support to research groups acting on modern themes with international impact. (AU)

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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)
AMARAL, MONICA F. Z. J.; BAUMGARTNER, AMANDA A.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Directed Metalation of 1-Ester-Substituted Indolizines: Base/Electrophile-Controlled Regioselective Functionalization. ORGANIC LETTERS, v. 17, n. 2, p. 238-241, . (13/04766-8, 11/20742-6)
Academic Publications
(References retrieved automatically from State of São Paulo Research Institutions)
TOLEDO, Mônica Franco Zannini Junqueira. Application of organometallic reagents in the functionalization of indolizines of synthetic interest. 2015. Doctoral Thesis - Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto (PCARP/BC) Ribeirão Preto.

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