199179-13-0Relevant articles and documents
Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,Fayne, Darren,McKeown, James P.,McCabe, Thomas,Twamley, Brendan,Williams, Clive,Meegan, Mary J.
, p. 181 - 199 (2018/03/13)
Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.
Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands
Barros, Cleiton Diniz,Amato, Angélica Amorim,Oliveira, Tiago Bento de,Iannini, Karime Bicas Rocha,Silva, Anekécia Lauro da,Silva, Teresinha Gon?alves da,Leite, Elisa Soares,Hernandes, Marcelo Zaldini,Lima, Maria do Carmo Alves de,Galdino, Suely Lins,Neves, Francisco de Assis Rocha,Pitta, Ivan da Rocha
experimental part, p. 3805 - 3811 (2010/08/06)
Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPARγ, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPARγ structure, which corroborates the hypothesis that these molecules are potential ligands of PPARγ. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPARγ, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromo-benzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-di one compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site.
Synthesis and schistosomicidal activity of new substituted thioxo-imidazolidine compounds
Albuquerque,Silva,Pitta,Silva,Silva,Malagueno,Santana,Wanderley,Lima,Galdino,Barbe,Pitta, Ivan Rocha
, p. 13 - 17 (2007/10/03)
Synthesis and physico-chemical properties of 3-benzyl-5-(4-fluoro- benzylidene)-1-methyl-2-thioxo-imidazolidin-4-ones, 5-benzylidene-3-(4-nitro- benzyl)-2-thioxo-imidazolidin-4-onesand4-acridin-9-ylmethylene-1-benzyl-5- thioxo-imidazolidin-2-ones compounds are described. These thioxo-imidazolidine derivatives were prepared by alkylation and condensation with 4-fluoro-benzaldehyde or nucleophilic Michael addition with cyanoacrylates. The schistosomicidal activity of 3-benzyl-5-(4-fluoro-benzylidene)-1-methyl-2- thioxo-imidazolidin-4-one compounds was evaluated.
Synthesis and anti-inflammatory activity of new thiazolidine-2,4-diones, 4-thioxothiazolidinones and 2-thioxoimidazolidinones
Santos,Uchoa,Canas,Sousa,Moura,Lima,Galdino,Pitta,Barbe
, p. 121 - 128 (2007/10/03)
New benzylidene imidazolidine and thiazolidine derivatives were prepared by nucleophilic addition on cyanoacrylates from substituted thioxoimidazolidinones, thiazolidinediones and thioxothiazolidinones. Anti-inflammatory activity of the synthesized thiazolidines was evaluated by the carrageenin-induced paw oedema test.
A novel way of synthesis of 1,3,5-trisubstituted-2-thioxoimidazolidinones
Brandao,Andrade,Pereira,Barbosa Filho,Lima,Galdino,Pitta,Barbe
, p. 9 - 14 (2007/10/03)
Title compounds were prepared by 1,4-nucleophilic addition of 2-thioxoimidazolidin-4-ones to 3-aryl-2-cyano acrylates, followed by alkylation. Reaction yield are much better than those obtained in case of Knoevenagel-type condensation.
