4 research outputs found
Functionalized Cyclopentenones with Low Electrophilic Character as Anticancer Agents
In this study were synthesized non-Michael acceptor cyclopentenones (CP) from biomass derivative furfural as anticancer agents. Cyclic enones, both from natural sources and synthetic analogues, have been described as cytotoxic agents. Most of these agents were unsuccessful in becoming valuable therapeutic agents due to toxicity problems derived from unselective critical biomacromolecule alkylation. This may be caused by Michael addition to the enone system. Ab initio studies revealed that 2,4-substituted CPs are less prone to Michael additions, and as such were tested three families of those derivatives. We prepare the new CPs from furfural through a tandem furan ring opening/nazarov electrocyclization and further functionalization. Experimentally the 2,4-substituted CPs exhibited no reactivity towards sulphur nucleophiles, while maintaining cytotoxicity against HT-29, MCF-7, NCI-H460, HCT-116 and MDA-MB 231 cells lines. Moreover, the selected CP are non-toxic against healthy HEK 293T cell lines and present proper calculated drug-like properties
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Unlocking the Potential of Bio‐Based Nitrogen‐Rich Furanic Platforms as Biomass Synthons
The demand for new biomass‐derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5‐hydroxymethylfurfural are cornerstones of sustainable chemistry, 3‐acetamido‐5‐acetyl furan (3A5AF), an N‐rich furan obtained from chitin biomass, remains unexplored, due to the poor reactivity of the acetyl group relative to previous furanic aldehydes. Here we developed a reactive 3‐acetamido‐5‐furfuryl aldehyde (3A5F) and demonstrated the utility of this synthon as a source of bio‐derived nitrogen‐rich heteroaromatics, carbocycles, and as a bioconjugation reagent
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Unlocking the Potential of Bio-Based Nitrogen-Rich Furanic Platforms as Biomass Synthons.
The demand for new biomass-derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5-hydroxymethylfurfural are cornerstones of sustainable chemistry, 3-acetamido-5-acetyl furan (3A5AF), an N-rich furan obtained from chitin biomass, remains unexplored, due to the poor reactivity of the acetyl group relative to previous furanic aldehydes. Here we developed a reactive 3-acetamido-5-furfuryl aldehyde (3A5F) and demonstrated the utility of this synthon as a source of bio-derived nitrogen-rich heteroaromatics, carbocycles, and as a bioconjugation reagent