57543-87-0Relevant articles and documents
Augmentation of Enantioselectivity by Spatial Tuning of Aminocatalyst: Synthesis of 2-Alkyl/aryl-3-nitro-2 H-chromenes by Tandem Oxa-Michael-Henry Reaction
Bez, Ghanashyam,Mohanta, Rahul
, p. 4627 - 4636 (2020/05/01)
The asymmetric oxa-Michael addition of salicylaldehyde to conjugated nitroalkenes often suffers from poor reactivity and selectivity and a long reaction time. Because of the formation of an iminium ion with aminocatalyst, the nucleophilicity of the phenol
One pot, three component synthesis of spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition
Nayak, Sabita,Pattanaik, Priyabrata,Mohapatra, Seetaram,Mishra, Deepak Ranjan,Panda, Pravati,Raiguru, Bishnuprasad,Mishra, Nilima Priyadarshini,Jena, Subhrakant,Biswal, Himansu Sekhar
supporting information, p. 1823 - 1835 (2019/05/15)
An expedient one-pot sequential three-component synthesis of a series of diverse spiroindenoquinoxaline pyrrolidine fused nitrochromene derivatives following 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the condensation of indenoqui
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.