Synthesis of calcogeno amino acids derivatives and 4-calcogeno quinolines via multicomponent reactions

• Grant number: 16/04289-3
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• Start date: June 01, 2016
• End date: April 30, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Isadora Maria de Oliveira
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

This project aims to develop multicomponent reactions for the synthesis of derivatives of 4-calcogenoquinolines (Povarov reaction or aza-Diels-Alder reaction) and ², ³-calcogenoalquinil-amino esters (coupling A3), for both will be used the same precursor reagents . It aims to assess the biological potential of the synthesized molecules. (AU)

Scientific publications

(14)

(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)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; STEFANI, HELIO A.. alpha,beta-Unsaturated 2-Ketoglycosides via Pd-Catalyzed Carbonylative Heck Reaction of 2-Iodoglycals. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2020, n. 32, JUL 2020. (16/24396-9, 16/04289-3, 17/26673-2, 14/50316-7, 17/24821-4)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Palladium-Catalyzed Thio- and Selenocarbonylation of 2-Iodoglycals. CHEMCATCHEM, v. 12, n. 2, NOV 2019. (16/24396-9, 16/04289-3, 17/26673-2, 17/24821-4)

DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; DE OLIVEIRA, ISADORA M.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction. RSC ADVANCES, v. 9, n. 17, p. 9468-9474, 2019. (17/26673-2, 16/04289-3, 17/24821-4, 16/02392-1, 16/24396-9)

VASCONCELOS, STANLEY N. S.; DE OLIVEIRA, ISADORA MARIA; SHAMIM, ANWAR; ZUKERMAN-SCHPECTOR, JULIO; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Stereoselective Oxa-Michael Addition of Tyrosine to Propargyl Aldehyde/Esters: Formation of Benzofurans and Flavones. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 18, JULY 2019. (13/17960-7, 16/04289-3)

VASCONCELOS, STANLEY N. S.; REIS, JOEL S.; DE OLIVEIRA, ISADORA M.; BALFOUR, MICHAEL N.; STEFANI, HELIO A.. Synthesis of symmetrical biaryl compounds by homocoupling reaction. Tetrahedron, v. 75, n. 13, p. 1865-1959, MAR 29 2019. (13/17960-7, 16/04289-3, 17/24821-4, 14/19221-0, 16/02392-1)

DE OLIVEIRA, ISADORA M.; DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Ytterbium-catalyzed formal [4+2] cycloaddition: Synthesis of chalcogen-quinolines 3-unsubstituted. Tetrahedron Letters, v. 59, n. 44, p. 3907-3911, OCT 31 2018. (16/04289-3, 17/26673-2, 16/24396-9)

DE OLIVEIRA, ISADORA M.; VASCONCELOS, STANLEY S. N.; BARBEIRO, CRISTIANE S.; CORRERA, THIAGO C.; SHAMIM, ANWAR; PIMENTA, DANIEL C.; CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines. NEW JOURNAL OF CHEMISTRY, v. 41, n. 18, p. 9884-9888, SEP 21 2017. (13/17960-7, 12/00424-2, 14/15962-5, 16/04289-3)

DE OLIVEIRA, ISADORA M.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.; MANARIN, FLAVIA. Copper(I)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A(3)-coupling. NEW JOURNAL OF CHEMISTRY, v. 42, n. 12, p. 10118-10123, JUN 21 2018. (16/04289-3)

DARBEM, MARIANA P.; KANNO, KARINA S.; DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of amidoglucals and glucal esters via carbonylative coupling reactions of 2-iodoglucal using Mo(CO)(6) as a CO source. NEW JOURNAL OF CHEMISTRY, v. 43, n. 2, p. 696-699, JAN 14 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

DE OLIVEIRA, ISADORA M.; ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; SARTORELLI, ARTHUR; CORRERA, THIAGO C.; RODRIGUES-OLIVEIRA, ANDRE F.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; MANARIN, FLAVIA; STEFANI, HELIO A.. Stereo- and Regioselective Cu-Catalyzed Hydroboration of Alkynyl Chalcogenoethers. CHEMCATCHEM, v. 12, n. 13, MAY 2020. (16/04289-3, 14/50316-7, 17/24821-4, 16/24396-9, 17/26673-2)

DE JESUS, DANIEL FELIPE FREITAS; DE FREITAS, ALINE LUIZA DUARTE; DE OLIVEIRA, ISADORA MARIA; DE ALMEIDA, LARISSA COSTA; BASTOS, RAFAEL WESLEY; SPADARI, CRISTINA DE CASTRO; MELO, ANALY SALES DE AZEVEDO; SANTOS, DANIEL DE ASSIS; COSTA-LOTUFO, LETICIA VERAS; REIS, FLAVIA C. G.; et al. Organoselenium Has a Potent Fungicidal Effect on Cryptococcus neoformans and Inhibits the Virulence Factors. Antimicrobial Agents and Chemotherapy, v. 67, n. 3, p. 16-pg., 2023-02-23. (16/04289-3, 17/15226-5, 21/01279-5, 18/12149-2, 20/00295-4, 15/17177-6)

DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, ANTONIO G.; STEFANI, HELIO A.; MANARIN, FLAVIA. Iron (III)-Promoted Synthesis of Substituted 4H-Chalcogenochromenes and Chemoselective Functionalization. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 13, p. 3163-3172, JUL 2 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

COSTA, CLAUDIA A.; LOPES, RAYSSA M.; FERRAZ, LETICIA S.; ESTEVES, GABRIELA N. N.; DI IORIO, JULIANA F.; SOUZA, ALINE A.; DE OLIVEIRA, ISADORA M.; MANARIN, FLAVIA; JUDICE, WAGNER A. S.; STEFANI, HELIO A.; et al. Cytotoxicity of 4-substituted quinoline derivatives: Anticancer and antileishmanial potential. Bioorganic & Medicinal Chemistry, v. 28, n. 11, JUN 1 2020. (16/04289-3, 18/25747-5, 16/25112-4, 17/24821-4, 14/02205-1)

BARBEIRO, CRISTIANE S.; VASCONCELOS, STANLEY N. S.; DE OLIVEIRA, ISADORA M.; ZUKERMAN-SCHPECTOR, JULIO; CARACELLI, IGNEZ; MAGANHI, STELLA H.; STEFANI, HELIO A.. Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by Palladium Complexes of Hydroxynaphthalene-2-Oxazolines. CHEMISTRYSELECT, v. 2, n. 26, p. 8173-8177, SEP 11 2017. (13/17960-7, 16/04289-3)

Academic Publications

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

OLIVEIRA, Isadora Maria de. Chalcogen-alkynes: Synthesis and application in multicomponent reactions to achieve quinolines, propargyl amines and vinyl β-borylated esters. 2020. Doctoral Thesis - Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ) São Paulo.