Research Grants 14/26378-2 - Síntese orgânica, Produtos naturais - BV FAPESP
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Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity

Abstract

The fine chemicals industry is entirely based on batch processes. Although the performance of batch reactors is well predictable, there are some limitations related to scale-up, reproducibility, safety, etc. The use of continuous processes by the fine chemicals industry is hampered mainly by financial and regulatory issues, however the high competitiveness of the industry and the pressure for a more sustainable manufacturing should boost a change of this paradigm. In this context, the use of continuous micro- and meso-reactors in the early stages of development stands as a promising alternative. Indeed, micro- and meso-reactors technology has been employed in the multi-step synthesis of molecules with high added value, particularly in academia. Micro- and meso-reactors offer significant advantages over traditional batch reactors such as faster and safer reactions, purer products, fast reaction optimization, easer scale up and integration of processes that are usually performed separately such as synthesis, purification and analysis. In this context, this proposal has as the main goal the establishment of a research group in the field of micro-reactor assisted organic synthesis. To achieve this goal, we intend to develop efficient methods for synthesis using micro and meso-reactors, aiming at the preparation of compounds with different properties and applications, such as natural products, drugs and new drug candidates. This proposal is strategically divided into sub projects that envolves (i) the development of new procedures for conjugate addition reactions and copper catalyzed allylic substitution reactions in continuous flow conditions, (ii) the synthesis of carbon nanotube supported organocatalyst aiming at its application to the addition of organozinc reagents to aldehydes and other organocatalyzed reactions, (iii) the development of methodologies for the ketene generation under continuous flow conditions and its application for multi step synthesis and (iv) the synthesis of biologically active natural products, such as goniothalamin, spilanthol, piplartine, cenocladamide and derivatives, using this platform for their preparation, aiming at surpassing limitations associated with the batch mode providing an alternative route. Also, this proposal aims to support further studies for the evaluation of the biological activity of the compounds prepared through the established collaborations with researchers from CPQBA / UNICAMP. (AU)

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Scientific publications (27)
(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)
FORNI, JOSE AUGUSTO; TONETO NOVAES, LUIZ FERNANDO; GALAVERNA, RENAN; PASTRE, JULIO C.. Novel polystyrene-immobilized chiral amino alcohols as heterogeneous ligands for the enantioselective arylation of aldehydes in batch and continuous flow regime. CATALYSIS TODAY, v. 308, n. SI, p. 86-93, . (14/26093-8, 15/08199-6, 14/25770-6, 14/26378-2)
PASTRE, JULIO C.; MURRAY, PHILIP R. D.; BROWNE, DUNCAN L.; BRANCAGLION, GUILHERME A.; GALAVERNA, RENAN S.; PILLI, RONALDO A.; LEY, V, STEVEN. Integrated Batch and Continuous Flow Process for the Synthesis of Goniothalamin. ACS OMEGA, v. 5, n. 29, p. 18472-18483, . (13/07607-8, 12/05909-4, 14/26378-2)
HERRERA, CHRISTIAN LEONARDO; SANTIAGO, JOAO VICTOR; PASTRE, JULIO CEZAR; CORREIA, CARLOS ROQUE DUARTE. In Tandem Auto-Sustainable Enantioselective Heck-Matsuda Reactions Directly from Anilines. ADVANCED SYNTHESIS & CATALYSIS, v. 364, n. 11, p. 10-pg., . (14/26378-2, 13/07600-3, 14/25770-6)
GALAVERNA, RENAN; BREITKREITZ, MARCIA C.; PASTRE, JULIO C.. Conversion of D-Fructose to 5-(Hydroxymethyl)furfural: Evaluating Batch and Continuous Flow Conditions by Design of Experiments and In-Line FTIR Monitoring. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. 6, n. 3, p. 4220-4230, . (14/25770-6, 16/05636-9, 06/57897-9, 14/26378-2, 13/07607-8)
DAMIAO, MARIANA C. F. C. B.; GALAVERNA, RENAN; KOZIKOWSKI, ALAN P.; EUBANKS, JAMES; PASTRE, JULIO C.. Telescoped continuous flow generation of a library of highly substituted 3-thio-1,2,4-triazoles. REACTION CHEMISTRY & ENGINEERING, v. 2, n. 6, p. 896-907, . (15/18572-6, 14/25770-6, 14/26378-2, 13/07607-8)
SANTOS, CARLA C. F.; PARADELA, LUCIANA S.; NOVAES, LUIZ F. T.; DIAS, SANDRA M. G.; PASTRE, JULIO C.. Design and synthesis of cenocladamide analogues and their evaluation against breast cancer cell lines. MedChemComm, v. 8, n. 4, p. 755-766, . (15/08199-6, 14/25770-6, 14/26378-2, 14/15968-3)
NOVAES, LUIZ F. T.; PASTRE, JULIO C.. Formal Total Synthesis of Actinoranone and Asymmetric Synthesis of Labda-7,13-(E)-dien-15-ol. ORGANIC LETTERS, v. 19, n. 12, p. 3163-3166, . (15/08199-6, 14/25770-6, 14/26378-2)
COSTA, RENNA K. E.; BRANCAGLION, GUILHERME A.; PINHEIRO, MATHEUS P.; ADAMOSKI, DOUGLAS; DA SILVA, BIANCA N.; NEGRAO, CYRO Z. DE V.; GONCALVES, KALIANDRA DE A.; RODRIGUES, CAMILA T.; AMBROSIO, ANDRE L. B.; GUIDO, RAFAEL V. C.; et al. Discovery of aminothiazole derivatives as a chemical scaffold for glutaminase inhibition. RESULTS IN CHEMISTRY, v. 5, p. 17-pg., . (13/07600-3, 16/09077-4, 21/13736-1, 14/26378-2, 19/16351-3, 20/12904-5, 21/06661-5, 14/15968-3)
GOMES, GUSTAVO R.; MATTIOLI, RENAN R.; PASTRE, JULIO CEZAR. Amino Acid-Based Deep Eutectic Solvents in Biomass Processing- Recent Advances. Journal of the Brazilian Chemical Society, v. 33, n. 8, p. 9-pg., . (14/26378-2, 19/26450-9, 18/09861-2, 14/25770-6, 20/11578-7)
FORNI, JOSE AUGUSTO; TONETO NOVAES, LUIZ FERNANDO; GALAVERNA, RENAN; PASTRE, JULIO C.. Novel polystyrene-immobilized chiral amino alcohols as heterogeneous ligands for the enantioselective arylation of aldehydes in batch and continuous flow regime. CATALYSIS TODAY, v. 308, p. 8-pg., . (15/08199-6, 14/26378-2, 14/25770-6, 14/26093-8)
GUSTAVO R. GOMES; RENAN R. MATTIOLI; JULIO CEZAR PASTRE. Amino Acid-Based Deep Eutectic Solvents in Biomass Processing - Recent Advances. Journal of the Brazilian Chemical Society, v. 33, n. 8, p. 815-823, . (18/09861-2, 19/26450-9, 14/25770-6, 14/26378-2, 20/11578-7)
DE SOUZA, JULIANA M.; GALAVERNA, RENAN; DE SOUZA, ALINE A. N.; BROCKSOM, TIMOTHY J.; PASTRE, JULIO C.; DE SOUZA, RODRIGO O. M. A.; DE OLIVEIRA, KLEBER T.. Impact of continuous flow chemistry in the synthesis of natural products and active pharmaceutical ingredients. Anais da Academia Brasileira de Ciências, v. 90, n. 2, p. 1131-1174, . (11/13993-2, 13/07276-1, 14/25770-6, 14/26378-2)
GOMES, GUSTAVO RODRIGUES; PASTRE, JULIO CEZAR. Microwave-assisted HMF production from water-soluble sugars using betaine-based natural deep eutectic solvents (NADES). SUSTAINABLE ENERGY & FUELS, v. 4, n. 4, p. 1891-1898, . (18/09861-2, 14/25770-6, 14/26378-2)
GOMES, GUSTAVO R.; SCOPEL, EUPIDIO; ROCHA, NICOLA L.; BREITKREITZ, MARCIA C.; CORMANICH, RODRIGO A.; REZENDE, CAMILA A.; PASTRE, JULIO C.. Direct Ethyl Levulinate Production from Raw Lignocellulosic Biomass Mediated by a Novel Taurine-Based Imidazolium Ionic Liquid. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. N/A, p. 13-pg., . (18/23769-1, 18/09861-2, 14/26378-2, 18/03910-1, 21/06661-5, 19/19360-3, 14/25770-6, 20/11578-7)
GALAVERNA, RENAN; MCBRIDE, TOM; PASTRE, JULIO C.; BROWNE, DUNCAN L.. Exploring the generation and use of acylketenes with continuous flow processes. REACTION CHEMISTRY & ENGINEERING, v. 4, n. 9, p. 1559-1564, . (14/25770-6, 14/26378-2)
ALONSO, ISABELLA G.; YAMANE, LAIS T.; DE FREITAS-BLANCO, VERONICA S.; NOVAES, LUIZ F. T.; FRANZ-MONTAN, MICHELLE; DE PAULA, ENEIDA; RODRIGUES, MARILI V. N.; RODRIGUES, RODNEY A. F.; PASTRE, JULIO C.. A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity. Tetrahedron, v. 74, n. 38, p. 5192-5199, . (15/08199-6, 14/06461-2, 14/25770-6, 14/16186-9, 14/26378-2)
SIVO, ALESSANDRA; GALAVERNA, RENAN DE SOUZA; GOMES, GUSTAVO RODRIGUES; PASTRE, JULIO CEZAR; VILE, GIANVITO. From circular synthesis to material manufacturing: advances, challenges, and future steps for using flow chemistry in novel application area. REACTION CHEMISTRY & ENGINEERING, v. 6, n. 5, p. 756-786, . (14/25770-6, 14/26378-2, 18/09861-2)
DAMIAO, MARIANA C. F. C. B.; MARCON, HENRIQUE M.; PASTRE, JULIO CEZAR. Continuous flow synthesis of the URAT1 inhibitor lesinurad. REACTION CHEMISTRY & ENGINEERING, v. 5, n. 5, p. 865-872, . (14/25770-6, 14/26378-2, 15/18572-6, 13/07607-8, 18/25233-1)
GALAVERNA, RENAN; RIBESSI, RAFAEL L.; ROHWEDDER, JARBAS J. R.; PASTRE, JULIO C.. Coupling Continuous Flow Microreactors to MicroNIR Spectroscopy: Ultracompact Device for Facile In-Line Reaction Monitoring. ORGANIC PROCESS RESEARCH & DEVELOPMENT, v. 22, n. 7, p. 780-788, . (14/50951-4, 14/26378-2, 14/25770-6, 13/07607-8)
NOVAES, LUIZ F. T.; GONCALVES, KALIANDRA DE ALMEIDA; TRIVELLA, DANIELA B. B.; PASTRE, JULIO C.. Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies. Journal of Organic Chemistry, v. 83, n. 9, p. 5160-5176, . (15/08199-6, 14/25770-6, 14/26378-2)
LUIZ F. T. NOVAES; JULIO C. PASTRE. AVANÇOS RECENTES NA HIDROAMINAÇÃO DE COMPOSTOS INSATURADOS. Química Nova, v. 40, n. 8, p. 932-945, . (14/25770-6, 15/08199-6, 14/26378-2)
GALAVERNA, RENAN; FERNANDES, LUCAS P.; BROWNE, DUNCAN L.; PASTRE, JULIO C.. Continuous flow processing as a tool for the generation of terpene-derived monomer libraries. REACTION CHEMISTRY & ENGINEERING, v. 4, n. 2, p. 362-367, . (14/25770-6, 14/26378-2)
GOMES, GUSTAVO RODRIGUES; BREITKREITZ, MARCIA CRISTINA; PASTRE, JULIO CEZAR. Ash Influence on the Ethyl Levulinate Production from Sugarcane Molasses Mediated by Taurine Hydrogen Sulfate. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. 9, n. 40, p. 13438-13449, . (14/25770-6, 20/11578-7, 18/09861-2, 14/26378-2)
GALAVERNA, RENAN S.; FERNANDES, LUCAS P.; DA SILVA, VITOR H. MENEZES; DE SIERVO, ABNER; PASTRE, JULIO C.. Humins-Like Solid Support for Palladium Immobilization: Highly Efficient and Recyclable Catalyst for Cross-Coupling Reactions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 24, p. 11-pg., . (14/26378-2, 14/25770-6, 20/11578-7)
DE SOUZA, JULIANA M.; GALAVERNA, RENAN; DE SOUZA, ALINE A. N.; BROCKSOM, TIMOTHY J.; PASTRE, JULIO C.; DE SOUZA, RODRIGO O. M. A.; DE OLIVEIRA, KLEBER T.. Impact of continuous flow chemistry in the synthesis of natural products and active pharmaceutical ingredients. Anais da Academia Brasileira de Ciências, v. 90, p. 44-pg., . (14/25770-6, 14/26378-2, 13/07276-1, 11/13993-2)
MARCON, HENRIQUE MAGRI; PASTRE, JULIO CEZAR. Continuous flow Meerwein-Ponndorf-Verley reduction of HMF and furfural using basic zirconium carbonate. RSC ADVANCES, v. 12, n. 13, p. 10-pg., . (14/26378-2, 18/25233-1, 14/25770-6, 20/11578-7)
GOMES, GUSTAVO R.; SCOPEL, EUPIDIO; BREITKREITZ, MARCIA C.; REZENDE, CAMILA A.; PASTRE, JULIO C.. Valorization of sugarcane bagasse C5-fraction by furfural production mediated by renewable glycine-based ionic liquid. INDUSTRIAL CROPS AND PRODUCTS, v. 191, p. 11-pg., . (18/09861-2, 18/23769-1, 14/26378-2, 21/06661-5, 20/11578-7, 19/19360-3, 14/25770-6)

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Filed patent(s) as a result of this research project

PROCESSO DE OBTENÇÃO DO ESPILANTOL E ANÁLOGOS, ESPILANTOL E ANÁLOGOS OBTIDOS BR1020160178711 - Universidade Estadual de Campinas (UNICAMP) . Júlio Cezar Pastre ; Isabella Gonçalves Alonso - July 2016, 29

COMPOSIÇÃO E FORMULAÇÃO TÓPICA ANESTÉSICA E SEU USO BR1020170113779 - Universidade Estadual de Campinas (UNICAMP) . Julio Cezar Pastre ; Marili Vila Nova Rodrigues ; Michelle Franz Montan Braga Leite ; Luiz Fernando Toneto Novaes ; Verônica Santana de Freitas Blanco ; Eneida de Paula ; Isabella Gonçalves Alonso ; Lais Thiemi Yamane ; Rodney Alexandre Ferreira Rodrigues - May 2017, 30

PROCESSO DE OBTENÇÃO DE ESPILANTOL BR1320190170386 - Universidade Estadual de Campinas (UNICAMP) . Júlio Cezar Pastre / GUILHERME ANDRADE BRANCAGLION / ISABELLA GONÇALVES ALONSO - August 2019, 15

PROCESSO DE OBTENÇÃO DO ESPILANTOL E ANÁLOGOS, ESPILANTOL E ANÁLOGOS OBTIDOS PCT/BR2017/000085 - Padtec S/A ; Universidade Estadual de Campinas (UNICAMP) . Julio Cezar Pastre ; Isabella Gonçalves Alonso - July 2017, 28