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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

Fabiane Gritzenco
a   Programa 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
b   Departamento de Química, Universidade Federal de Santa Maria-UFSM, 97105-900 Santa Maria, RS, Brazil
,
Thiago Anjos 
b   Departamento de Química, Universidade Federal de Santa Maria-UFSM, 97105-900 Santa Maria, RS, Brazil
,
Adriane Sperança
c   Instituto Federal Farroupilha, Santo Ângelo, RS, Brazil
,
Maura L. B. Peixoto
d   Escola de Química e Alimentos, Universidade Federal do Rio Grande, Campus Santo Antônio da Patrulha, RS, Brazil
,
Marcelo Godoi
d   Escola de Química e Alimentos, Universidade Federal do Rio Grande, Campus Santo Antônio da Patrulha, RS, Brazil
,
Kauane N. B. Ledebuhr
e   Laboratório 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
e   Laboratório 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
a   Programa 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  ∗
a   Programa 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
› Author AffiliationsFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (PRONEM­ 16/2551-0000240-1 and PRONEX 16/2551) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (Universal - Processo 428193/2018-8). This study was financed in part by the Coordenação­ de Aperfeiçoamento de Pessoal de Nível Superior - Brazil­ (CAPES) - Finance Code 001.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1477-6470.
  • Supporting Information


Publication History

Received: 06 March 2021

Accepted after revision: 08 April 2021

Accepted Manuscript online:
08 April 2021

Article published online:
26 April 2021

© 2021. Thieme. All rights reserved

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