Greener approach for the synthesis of nitrovinylfurans from biomass-derived 5-hydroxymethyfurfural as selective antiproliferative agents

• Published in: Sustainable chemistry and pharmacy Vol. 30; p. 100828
• Main Authors: Ortiz, Federico, Tassano, Tiago, Ingold, Mariana, de la Sovera, Victoria, Puerta, Adrián, Padrón, José M., López, Gloria V., Porcal, Williams
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.12.2022
• Subjects: 5-Hydroxymethylfurfural; Antiproliferative activity; Biomass-derived; Greener synthesis; Nitrovinylfuran; Biomass-derived; Greener synthesis; Antiproliferative activity; Nitrovinylfuran; 5-Hydroxymethylfurfural
• ISSN: 2352-5541; 2352-5541
• DOI: 10.1016/j.scp.2022.100828

Biomass-derived chemical platforms such as 5-hydroxymethylfurfural (5-HMF) can offer straightforward access to new value-added products. The presence of an aldehyde and hydroxymethyl functional groups in this molecule are interesting structural motifs to explore the synthesis of new bioactive compounds. In this contribution, a strategy to quickly and efficiently synthesize nitrovinylfurans starting from 5-HMF under greener conditions is described and the antiproliferative activity of the synthesized compounds evaluated. 5-HMF obtained by microwave-assisted saturated biphasic dehydration from fructose was used to produce furaldehyde derivatives. Next, through a nitroaldolic condensation, the desired nitrovinylfurans were generated using efficient heating sources, ultrasound, or a non-microwave instant heating reactor, under solvent-free conditions. Most of the newly synthesized compounds showed growth inhibition when assayed for their in vitro antiproliferative activity against six cancer cell lines (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), with lower toxicity on the human macrophage-like cells (THP-1). Our strategy allowed the rapid identification of nitrovinylfurans 16, 17, 19, and 20 as future candidates for the development of new selective anticancer drugs. [Display omitted] •Greener synthesis of nitrovinylfurans from biomass-derived 5-hydroxymethyfurfural.•Microwave-assisted synthesis of 5-HMF from fructose achieved in a short reaction time by a simple and efficient protocol.•Nitroaldolic condensation achieved under efficient heating and solvent-free conditions.•Cytotoxicity tested on 6 cancer cell lines and human macrophages-like cells.•New nitrovinylfurans with remarkable selectivity towards tumor cells were obtained.