Antioxidant activity of diphenylpropionamide derivatives: synthesis, biological evaluation and computational analysis

• Published in: Molecules (Basel, Switzerland) Switzerland), 2008-03, Vol.13 (4), p.749-761
• Main Authors: Urbani, Paolo, Ramunno, Anna, Filosa, Rosanna, Pinto, Aldo, Popolo, Ada, Bianchino, Erminia, Piotto, Stefano, Saturnino, Carmela, De Prisco, Rocco, Nicolaus, Barbara, Tommonaro, Giuseppina
• Format: Article
• Language: English
• Subjects: Acids; Amides - chemical synthesis; Amides - chemistry; Amides - pharmacology; Animals; antioxidant activity; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; antiproliferative activity; Bioassays; Biological activity; brine shrimp test; Cell Proliferation - drug effects; Computational Biology - methods; Cytotoxicity; Diphenylpropionamide derivatives; Lipopolysaccharides - pharmacology; Macrophages - cytology; Macrophages - drug effects; Mice; Nitrates; Nitric Oxide - metabolism; Propionates - chemical synthesis; Propionates - chemistry; Propionates - pharmacology; QSAR analysis; Reactive Oxygen Species - metabolism
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules13040749

We report the synthesis, antioxidant and antiproliferative activity and a QSAR analysis of synthetic diphenylpropionamide derivatives. Synthesis of these compounds was achieved by direct condensation of 2,2- and 3,3-diphenylpropionic acid and appropriate amines using 1-propylphoshonic acid cyclic anhydride (PPAA) as catalyst. Compound structures were elucidated by NMR analysis and their melting points were measured. The in vitro antioxidant activity of these compounds was tested by evaluating the amount of scavenged ABTS radical and estimating ROS and NO production in LPS stimulated J774.A1 macrophages. All compounds were tested for their effect on viability of cells and results demonstrated that they are not toxic towards the cell lines used. The cytotoxic activity of all compounds was evaluated by a Brine Shrimp Test.