Síntese de pequenas bibliotecas empregando organotrifluoroboratos de potássio em reações de Suzuki-Miyaura

• Processo: 12/00424-2
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Vigência: 01 de agosto de 2012 - 30 de novembro de 2016
• Área do conhecimento: Ciências Exatas e da Terra - Química - Química Orgânica
• Pesquisador responsável: Helio Alexandre Stefani
• Beneficiário: Helio Alexandre Stefani
• Instituição Sede: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brasil
• Pesquisadores associados: Ignez Caracelli ; Julio Zukerman Schpector ; Sandra Helena Poliselli Farsky
• Bolsa(s) vinculada(s): 16/05260-9 - Síntese e funcionalização de iodeto de sulfóxidos vinílicos, BP.DD; 13/21925-2 - 2-Aril/Heteroariloxazolinas: Síntese, Atividade Biológica e Fluorescência, BP.PD; 13/17960-7 - Funcionalização da 3-Iodo-(L)-Tirosina via Reação de Suzuki-Miyaura Empregando Organotrifluoroboratos de Potássio, BP.DR; + mais bolsas vinculadas 13/20553-4 - Síntese e funcionalização de iodeto de sulfóxidos vinílicos, BP.DD; 12/17954-4 - Reações de Ciclização de Acetil- e Etoxil-pirrolidin-2-onas com Sais de Organotrifluoroboratos de Potássio, BP.PD; 12/20483-3 - Reações de Adição 1,2 Empregando Sais de Organotrifluoroboratos de Potássio e a Imina do Etil Glioxalato (subprojeto 3 do temático), BP.PD - menos bolsas vinculadas
• Assunto(s): Compostos organometálicos
• Palavra(s)-Chave do Pesquisador: Haletos orgânicos | organometálicos | Organotrifluoroboratos de Potássio | reações de acoplamento | Suzuki-Miyaura | Organometálicos

Resumo

O projeto tem como tema principal, porém não exclusivo, o emprego de sais de organotrifluoroboratos de potássio (espécies nucleofílicas) na formação de ligações carbono-carbono (ligações sp2-sp2, sp2-sp, sp-sp) com haletos orgânicos e espécies insaturadas de telúrio (espécies eletrofílicas), esta última como alternativa aos haletos orgânicos tradicionais, catalisadas por um complexo de metal de transição. Visa o desenvolvimento de reações tipo Suzuki-Miyaura ou outras que sejam viáveis ao uso desta classe de reagentes e a obtenção de pequenas bibliotecas de compostos para disponibilização para testes biológicos. (AU)

Publicações científicas

(34)

(Referências obtidas automaticamente do Web of Science e do SciELO, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores)

VASCONCELOS, STANLEY N. S.; MEISSNER, KAMILA A.; FERRAZ, WITOR R.; TROSSINI, GUSTAVO H. G.; WRENGER, CARSTEN; STEFANI, HELIO A.. Indole-3-glyoxyl tyrosine: synthesis and antimalarial activity against Plasmodium falciparum. Future Medicinal Chemistry, v. 11, n. 6, p. 525-538, MAR 2019. (13/17960-7, 12/12807-3, 15/26722-8, 12/00424-2, 17/25543-8, 16/24790-9)

VASCONCELOS, STANLEY N. S.; BARBEIRO, CRISTIANE S.; KHAN, AMNA N.; STEFANI, HELIO A.. Synthesis of Biphenyl Tyrosine Via Cross-Coupling Suzuki-Miyaura Reaction Using Aryltrifluoroborate Salts. Journal of the Brazilian Chemical Society, v. 26, n. 4, p. 765-774, APR 2015. (13/17960-7, 12/00424-2, 12/20483-3)

VASCONCELOS, STANLEY N. S.; DREWES, CARINE C.; KANDA KUPA, LEONARD DE VINCI; FARSKY, SANDRA H. P.; STEFANI, HELIO A.. Evaluation of toxicity on epithelial and tumor cells of biaryl dipeptide tyrosines. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 114, p. 1-7, MAY 23 2016. (13/17960-7, 12/00424-2, 10/19802-1)

VASCONCELOS, STANLEY N. S.; MENEZES DA SILVA, VITOR H.; BRAGA, ATAUALPA A. C.; SHAMIM, ANWAR; SOUZA, FREDERICO B.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. 3-Alkenyltyrosines Accessed by Suzuki-Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions. ASIAN JOURNAL OF ORGANIC CHEMISTRY, v. 6, n. 7, p. 913-920, JUL 2017. (13/17960-7, 12/00424-2, 15/01491-3, 13/04813-6, 15/11840-5)

KHAN, AMNA N.; VASCONCELOS, STANLEY N. S.; CARRAU, GONZALO; STEFANI, HELIO A.. Microwave-Assisted Synthesis of beta-1,2,3-Triazolyl-alpha-amino Esters. Journal of the Brazilian Chemical Society, v. 26, n. 7, p. 1457-1465, JUL 2015. (12/00424-2, 12/20483-3)

SOUZA, FREDERICO B.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Microwave-assisted one-pot three-component synthesis of imine 1,2,3-triazoles. Tetrahedron Letters, v. 57, n. 14, p. 1592-1596, APR 6 2016. (13/20553-4, 12/00424-2)

VASCONCELOS, STANLEY N. S.; SHAMIM, ANWAR; ALI, BAKHAT; DE OLIVEIRA, ISADORA M.; STEFANI, HELIO A.. Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine. MOLECULAR DIVERSITY, v. 20, n. 2, p. 469-481, MAY 2016. (13/17960-7, 12/00424-2)

ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; WULF, GLAUDESTON DUTRA; STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; NG, SEIK WENG; TIEKINK, EDWARD R. T.. Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers. Molecules, v. 19, n. 2, p. 1990-2003, FEB 2014. (12/00424-2)

SHAMIM, ANWAR; SOUZA, FREDERICO B.; TROSSINI, GUSTAVO H. G.; GATTI, FERNANDO M.; STEFANI, HELIO A.. Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal. MOLECULAR DIVERSITY, v. 19, n. 3, p. 423-434, AUG 2015. (13/20553-4, 12/00424-2)

SHAMIM, ANWAR; SOUZA, FREDERICO B.; VASCONCELOS, STANLEY N. S.; STEFANI, HELIO A.. Synthesis of a library of glucal-derived triazoles via copper-catalyzed azide-alkyne cyclization. Tetrahedron Letters, v. 58, n. 9, p. 884-888, MAR 1 2017. (12/00424-2)

SOUZA, FREDERICO B.; SHAMIM, ANWAR; ARGOMEDO, LUIZ M. Z.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of enyne and aryl vinyl sulfoxides: functionalization via Pummerer rearrangement. MOLECULAR DIVERSITY, v. 19, n. 4, p. 773-785, NOV 2015. (13/20553-4, 12/00424-2, 11/11499-0)

SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; ALI, BAKHAT; MADUREIRA, LUCAS SOUSA; ZUKERMAN-SCHPECTOR, J.; STEFANI, HELIO A.. Ligand and copper free Sonogashira coupling to achieve 2-alkynyl D-glucal derivatives: regioselective electrophile promoted nucleophilic 5-endo-dig cyclization. Tetrahedron Letters, v. 56, n. 43, p. 5836-5842, OCT 21 2015. (12/00424-2)

CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; MAGANHI, STELLA H.; STEFANI, HELIO A.; GUADAGNIN, RAFAEL C.; TIEKINK, EDWARD R. T.. Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, v. 231, n. 6, p. 321-328, JUN 2016. (12/00424-2, 12/22524-9)

ZUKERMAN-SCHPECTOR, JULIO; MADUREIRA, LUCAS SOUSA; STEFANI, HELIO A.; GOZHINA, OLGA; TIEKINK, EDWARD R. T.. Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, v. 231, n. 6, p. 329-339, JUN 2016. (12/00424-2)

STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; MANARIN, FLAVIA; LEAL, DAIANA M.; SOUZA, FREDERICO B.; MADUREIRA, LUCAS SOUSA; ZUKERMAN-SCHPECTOR, JULIO; EBERLIN, MARCOS N.; GODOI, MARLA N.; GALAVERNA, RENAN DE SOUZA. Synthesis of 5-Organotellanyl-1H-1,2,3-triazoles: Functionalization of the 5-Position Scaffold by the Sonogashira Cross-Coupling Reaction. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2013, n. 18, p. 3780-3785, JUN 2013. (12/00424-2, 10/15677-8)

STEFANI, HELIO A.; MANARIN, FLAVIA; KHAN, AMNA N.; VASCONCELOS, STANLEY N. S.. Ytterbium(III)-Catalyzed Addition Reaction of Alkynyltrifluoroborate Salts to alpha-Imino Esters: Efficient Synthesis of beta-Unsaturated alpha-Amino Esters. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2014, n. 6, p. 1236-1240, FEB 2014. (12/00424-2)

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)

AMNA N. KHAN; STANLEY N. S. VASCONCELOS; GONZALO CARRAU; HÉLIO A. STEFANI. Microwave-Assisted Synthesis of β-1,2,3-Triazolyl-α-amino Esters. Journal of the Brazilian Chemical Society, v. 26, n. 7, p. 1457-1465, 2015-07-00. (12/20483-3, 12/00424-2)

STEFANI, HELIO A.; MANARIN, FLAVIA; SOUSA, ARIANE C. S.; SOUZA, FREDERICO B.; FERRAZ, WITOR RIBEIRO. Three-component reaction for the synthesis of diverse beta-unsaturated alpha-amino esters. Tetrahedron, v. 70, n. 20, p. 3243-3248, MAY 20 2014. (12/00424-2)

STEFANI, HELIO A.; ALI, BAKHAT; FERREIRA, FERNANDO P.. Ultrasound-assisted addition of alcohols to N-acyliminium ions mediated by In(OTf)3 and synthesis of 1,2,3-triazoles. Tetrahedron Letters, v. 55, n. 23, p. 3400-3405, JUN 4 2014. (12/00424-2, 12/17954-4)

STEFANI, HELIO A.; KHAN, AMNA N.; MANARIN, FLAVIA; VENDRAMINI, PEDRO H.; EBERLIN, MARCOS N.. Synthesis of alpha-alkenyl-alpha-amino esters via addition of potassium Alkenyltrifluoroborate salts to imine in the presence of Yb(OTf)(3). Tetrahedron Letters, v. 54, n. 46, p. 6204-6207, NOV 13 2013. (12/00424-2, 10/15677-8)

STEFANI, HELIO A.; VASCONCELOS, STANLEY N. S.; SOUZA, FREDERICO B.; MANARIN, FLAVIA; ZUKERMAN-SCHPECTOR, JULIO. One-pot three-component synthesis of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles. Tetrahedron Letters, v. 54, n. 43, p. 5821-5825, OCT 23 2013. (12/00424-2)

SHAMIM, ANWAR; BARBEIRO, CRIATIANE S.; ALI, BAKHAT; STEFANI, HELIO A.. Synthesis of Stannyl-Substituted D-Glucal Derivatives via Palladium-Catalyzed Regioselective Hydrostannation and Their Synthetic Applications. CHEMISTRYSELECT, v. 1, n. 18, p. 5653-5659, NOV 1 2016. (12/00424-2, 12/17954-4)

SOUZA, FREDERICO B.; VASCONCELOS, STANLEY N. S.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO. Synthesis and functionalization of N-sulfinyl imines: Sonogashira reaction and copper-catalyzed azide-alkyne cycloaddition. Tetrahedron Letters, v. 58, n. 11, p. 1057-1060, MAR 15 2017. (12/00424-2, 16/05260-9)

BALFOUR, MICHAEL N.; FRANCO, CAIO H.; MORAES, CAROLINA B.; FREITAS-JUNIOR, LUCIO H.; STEFANI, HELIO A.. Synthesis and trypanocidal activity of a library of 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 128, p. 202-212, MAR 10 2017. (12/00424-2)

VASCONCELOS, STANLEY N. S.; BELTRAN RODRIGUES, ANA CLARA; BASTOS, ERICK LEITE; STEFANI, HELIO A.. Synthesis of a Tyr-Tyr Peptide Library and Fluorescence of the Stilbenyl Derivatives. CHEMISTRYSELECT, v. 1, n. 6, p. 1287-1291, MAY 1 2016. (14/14866-2, 12/00424-2, 13/17960-7)

ALI, BAKHAT; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, FERNANDO P.; SHAMIM, ANWAR; PIMENTA, DANIEL C.; STEFANI, HELICI A.. Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes. Tetrahedron Letters, v. 56, n. 9, p. 1153-1158, FEB 25 2015. (12/00424-2, 12/17954-4, 11/11499-0)

STEFANI, HELIO A.; FERREIRA, FERNANDO P.; ALI, BAKHAT; PIMENTA, DANIEL C.. Synthesis of functionalized N-triazolyl maleimides. Tetrahedron Letters, v. 55, n. 31, p. 4355-4358, JUL 30 2014. (12/00424-2, 12/17954-4)

STEFANI, HELIO A.; SILVA, NATHALIA C. S.; VASCONCELOS, STANLEY N. S.; MANARIN, FLAVIA; SOUZA, FREDERICO B.. Functionalization of 5-telluro-1,2,3-triazoles: Te/Li exchange and Suzuki-Miyaura cross-coupling reaction. Tetrahedron Letters, v. 54, n. 22, p. 2809-2812, MAY 29 2013. (12/00424-2, 10/15677-8)

ALI, BAKHAT; SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; STEFANI, HELIO A.. Synthesis and applications of 4-substituted 1-(4-iodophenyl)pyrrolidine-2,5-diones. Tetrahedron Letters, v. 56, n. 28, p. 4234-4241, JUL 8 2015. (12/00424-2, 12/17954-4)

ALI, BAKHAT; VASCONCELOS, STANLEY N. S.; SHAMIM, ANWAR; ZUKERMAN-SCHPECTOR, J.; STEFANI, HELIO A.. Synthesis of 1-((4-methoxyphenyl)-3-alkynes)-1H-pyrrole-2,5-diones and functionalization to triazoles. ARABIAN JOURNAL OF CHEMISTRY, v. 10, n. 4, p. 500-508, MAY 2017. (12/00424-2, 12/17954-4, 13/17960-7)

ALI, BAKAT; KUPA, LEONARD D. KANDA; HELUANY, CINTIA S.; DREWES, CARINE C.; VASCONCELOS, STANLEY N. S.; FARSKY, SANDRA H. P.; STEFANI, HELIO A.. Cytotoxic effects of a novel maleimide derivative on epithelial and tumor cells. BIOORGANIC CHEMISTRY, v. 72, p. 199-207, JUN 2017. (13/17960-7, 12/17954-4, 12/00424-2, 10/19802-1, 14/07328-4)

VASCONCELOS, STANLEY N. S.; FORNARI, EVELIN; CARACELLI, IGNEZ; STEFANI, HELIO A.. Synthesis of alpha-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles. MOLECULAR DIVERSITY, v. 21, n. 4, p. 893-902, NOV 2017. (13/17960-7, 12/00424-2)

SHAMIM, ANWAR; VASCONCELOS, STANLEY N. S.; DE OLIVEIRA, ISADORA MARIA; REIS, JOEL S.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.. Synthesis of Glycosyl Azides and Their Applications Using CuAAC Click Chemistry to Generate Bis- and Tris(triazolyl)glycosyl Derivatives. SYNTHESIS-STUTTGART, v. 49, n. 23, p. 5183-5196, DEC 2017. (12/00424-2)