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

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

Publication History

Received: 06 March 2021

Accepted after revision: 08 April 2021

Accepted Manuscript online:
08 April 2021

Article published online:
26 April 2021

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