100668-11-9Relevant academic research and scientific papers
Combined dual effect of modulation of human neutrophils’ oxidative burst and inhibition of colon cancer cells proliferation by hydroxycinnamic acid derivatives
Tavares-da-Silva, Elisiário J.,Varela, Carla L.,Pires, Ana S.,Encarna??o, Jo?o C.,Abrantes, Ana M.,Botelho, Maria F.,Carvalho, Rui A.,Proen?a, Carina,Freitas, Marisa,Fernandes, Eduarda,Roleira, Fernanda M.F.
, p. 3556 - 3564 (2016)
Colon cancer is one of the most incident cancers in the Western World. While both genetic and epigenetic factors may contribute to the development of colon cancer, it is known that chronic inflammation associated to excessive production of reactive oxygen and nitrogen species by phagocytes may ultimately initiate the multistep process of colon cancer development. Phenolic compounds, which reveal antioxidant and antiproliferative activities in colon cancer cells, can be a good approach to surpass this problem. In this work, hydroxycinnamic amides and the respective acid precursors were tested in vitro for their capacity to modulate human neutrophils’ oxidative burst and simultaneously to inhibit growth of colon cancer cells. A phenolic amide derivative, caffeic acid hexylamide (CAHA) (4) was found to be the most active compound in both assays, inhibiting human neutrophils’ oxidative burst, restraining the inflammatory process, inhibiting growth of colon cancer cells and triggering mitochondrial dysfunction that leads cancer cells to apoptosis. Altogether, these achievements can contribute to the understanding of the relationship between antioxidant and anticancer activities and based on the structure–activity relationships (SAR) established can be the starting point to find more effective phenolic compounds as anticancer agents.
Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties
Roleira, Fernanda M.F.,Siquet, Christophe,Orr, Elizabeta,Garrido, E. Manuela,Garrido, Jorge,Milhazes, Nuno,Podda, Gianni,Paiva-Martins, Fátima,Reis, Salette,Carvalho, Rui A.,Silva, Elisiário J. Tavares Da,Borges, Fernanda
, p. 5816 - 5825 (2010)
Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure-property-
Lipase-Catalyzed Solvent-Free Amidation of Phenolic Acids
Kaushik, Parshant,Shakil, Najam Akhtar,Kumar, Jitendra,Singh, Braj Bhushan
supporting information, p. 579 - 587 (2015/10/29)
A series of N-alkyl-substituted amides, based on various phenolic acids, have been synthesized by the condensation of equimolar amounts of phenolic acids with different alkyl amines in the presence of Candida antarctica lipase at 60-90 °C in 16-20 h. The reactions were carried out in a solvent-free system without the use of any activating agents. All the products were obtained in appreciable amounts and the yields for different compounds varied between 75.6% and 83.5%. The synthesized compounds were characterized using spectroscopy techniques, namely infrared and NMR (1H and 13C). GRAPHICAL ABSTRACT.
