Diacetate Naphthoquinone Derivatives Tethered to 1,2,3-Triazoles: Synthesis and Cytotoxicity Evaluation in Caco-2 Cells

AUTOR(ES)

Costa, Dora C. S.; Francisco, Adriane S.; Matuck, Beatriz V. A.; Furtado, Priscila S.; Oliveira, Alana A. S. C. de; Rabelo, Vitor W.-H.; Sathler, Plínio C.; Abreu, Paula A.; Ferreira, Vitor F.; Silva, Luiz Cláudio R. P. da; Silva, Fernando C. da

FONTE

Journal of the Brazilian Chemical Society

DATA DE PUBLICAÇÃO

2022

RESUMO

Acetylated compounds prepared from naphthoquinones have been reported as antitumoral prodrugs. Exploring the synthetic versatility of the naphthoquinone and triazolic nuclei, herein we report a simple and efficient synthetic route to prepare a series of sixteen prodrugs prototype of 1,2,3-triazoles-naphthoquinodoic acetyl derivatives. The compounds 10a-10h and 11a-11h were obtained by oxidative cycloaddition reaction between lawsone and 4-vinyl-1H-1,2,3-triazoles promoted by ceric ammonium nitrate (CAN) in alkaline medium followed by reductive acetylation of the quinones in excess of metallic zinc and acetic anhydride in yields up to > 98%. All derivatives revealed to be hemocompatible and the compound 11e exhibited the most promising profile against Caco-2 cells showing the higher selectivity index. Molecular docking suggests that these compounds could exert their cytotoxic activity through inhibition of one topoisomerase II isoform, at least.

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