Base-Free Synthesis and Synthetic Applications of Novel 3-(Organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents

Fabiane Gritzenco; Jean C. Kazmierczak; Thiago Anjos; Adriane Sperança; Maura L. B. Peixoto; Marcelo Godoi; Kauane N. B. Ledebuhr; César Augusto Brüning; Lauren L. Zamin; Benhur Godoi

doi:10.1055/a-1477-6470

Synthesis, Table of Contents

Synthesis 2021; 53(15): 2676-2688
DOI: 10.1055/a-1477-6470

paper

Base-Free Synthesis and Synthetic Applications of Novel 3-(Organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents

Authors

Fabiane Gritzenco

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo 97900-000, RS, Brazil
Jean C. Kazmierczak

^bDepartamento de Química, Universidade Federal de Santa Maria-UFSM, 97105-900 Santa Maria, RS, Brazil
Thiago Anjos

^bDepartamento de Química, Universidade Federal de Santa Maria-UFSM, 97105-900 Santa Maria, RS, Brazil
Adriane Sperança

^cInstituto Federal Farroupilha, Santo Ângelo, RS, Brazil
Maura L. B. Peixoto

^dEscola de Química e Alimentos, Universidade Federal do Rio Grande, Campus Santo Antônio da Patrulha, RS, Brazil
Marcelo Godoi

^dEscola de Química e Alimentos, Universidade Federal do Rio Grande, Campus Santo Antônio da Patrulha, RS, Brazil
Kauane N. B. Ledebuhr

^eLaboratório de Bioquímica e Neurofarmacologia Molecular, Programa de Pós-Graduação em Bioquímica e Bioprospecção, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Pelotas, RS, Brazil
César Augusto Brüning

^eLaboratório de Bioquímica e Neurofarmacologia Molecular, Programa de Pós-Graduação em Bioquímica e Bioprospecção, Centro de Ciências Químicas, Farmacêuticas e de Alimentos, Universidade Federal de Pelotas, Pelotas, RS, Brazil
Lauren L. Zamin

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo 97900-000, RS, Brazil
Benhur Godoi ∗

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo 97900-000, RS, Brazil

Abstract

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Abstract

This manuscript portrays the CuI-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynyl esters and diorganyl dichalcogenides by using DMSO as solvent, at room temperature, under base-free and open-to-air atmosphere conditions. Generally, the reactions have proceeded very smoothly, being tolerant to a range of substituents present in both substrates, affording the novel 3-(organochalcogenyl)prop-2-yn-1-yl esters in moderate to good yields. Noteworthy, the 3-(butylselanyl)prop-2-yn-1-yl benzoate proved to be useful as synthetic precursor in palladium-catalyzed Suzuki and Sonogashira type cross-coupling reactions by replacing the carbon–chalcogen bond by new carbon–carbon bond. Moreover, the 3-(phenylselanyl)prop-2-yn-1-yl benzoate has shown promising in vitro activity against glioblastoma cancer cells.

Key words

organochalcogens - copper - catalysis - cross-coupling - glioblastoma

Full Text

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