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Application and development of continuous flow processes in the synthesis of fentanylic opioids

Grant number: 16/12718-1
Support Opportunities:Scholarships in Brazil - Doctorate (Direct)
Effective date (Start): August 01, 2016
Effective date (End): January 31, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Giuliano Cesar Clososki
Grantee:Artur de Lara Lima Vaz
Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil


In the past few years, organic synthesis in continuous flow has become a powerful tool in mid and large-scale production of Active Pharmaceutical Ingredients (APIs) in reduced spaces. In this context, the following project focus in the search for solutions in the synthesis of API precursors scaffolds by developing continuous flow protocols compatible with classic organic synthesis strategies, such as multicomponent reactions and use of organometallic intermediates. Specifically, the scientific activities will be directed on obtaining analgesic opioids analogue to Fentanyl, including 4-anilidopiperidines, 4-acyl-4-anilidopiperidines and 4-aryl-4-anilidopiperidines, which are of great importance in the therapy of pain related to many conditions, including cancer. While developing continuous flow methodologies, we expect to be able to provide fentanyl analogues in preparative scale, as this is a crucial step in establishing innovative processes in the pharmaceutical industry. Finally, in addition to furnishing compounds of known therapeutic importance, the project will allow for the preparation of novel fentanyl analogues with structural diversity that, after biological evaluation, could expand the current knowledge involving structure-activity relationships of this important class of compounds. (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)
NISHIMURA, RODOLFO H. V.; VAZ, ARTUR DE L. L.; BOZZINI, LEANDRO A.; MURIE, VALTER E.; CLOSOSKI, GIULIANO C.. Recent applications of magnesium- and Zinc-TMP amides in the synthesis of bioactive targets. Tetrahedron, v. 75, n. 4, p. 464-474, . (16/12718-1, 15/21364-6, 15/01466-9, 18/14150-8)
LIMA, RAFAELY N.; DE L. L. VAZ, ARTUR; CLOSOSKI, GIULIANO C.; PORTO, ANDRE L. M.. Sustainable Synthesis of Amides from Ethyl 3-(4-Hydroxyphenyl) Propionate. CHEMISTRYSELECT, v. 6, n. 13, p. 3271-3276, . (14/18257-0, 18/14150-8, 16/12718-1)

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