Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts

• Grant number: 13/17960-7
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: December 01, 2013
• End date: November 30, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Stanley Nunes Siqueira Vasconcelos
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• Associated research grant: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions, AP.TEM

Abstract

The project aims at the synthesis and functionalization of derivatives (L)-tyrosine from the reaction of potassium organotrifluoroborate salts and 3-iodo-(L)-tyrosine and biological evaluation of the synthesized products.

Scientific publications

(15)

(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)

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)

VASCONCELOS, STANLEY N. S.; SCIANI, JULIANA M.; LISBOA, NICOLE M.; STEFANI, HELIO A.. Synthesis of a Tyr-Tyr Dipeptide Library and Evaluation Against Tumor Cells. Medicinal Chemistry, v. 14, n. 7, p. 709-714, 2018. (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)

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)

BARBEIRO, CRISTIANE S.; VASCONCELOS, STANLEY N. S.; ZUKERMAN-SCHPECTOR, JULIO; CARACELLI, IGNEZ; PIMENTA, DANIEL C.; RODRIGUES, ANA CLARA B.; FERNANDES, ANDRE S.; CORRERA, THIAGO C.; BASTOS, ERICK L.; STEFANI, HELIO A.. Chlorinated 2-hydroxynaphthalenoxazolines: Synthesis, Reaction Mechanism and Fluorescence Properties. CHEMISTRYSELECT, v. 1, n. 18, p. 5647-5652, NOV 1 2016. (13/17960-7, 14/15962-5, 15/11769-9)

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)

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)

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.; 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)

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)

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)

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)

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)

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)

Academic Publications

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

VASCONCELOS, Stanley Nunes Siqueira. Tyrosine, a building block in cross-coupling reactions: synthesis of dipeptides Tyr-Tyr, heterocycles and biological activity investigations against cancer cells and parasidic cells. 2017. Doctoral Thesis - Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ) São Paulo.