105849-85-2Relevant academic research and scientific papers
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
, p. 1823 - 1835 (2019)
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.
Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives
Climent, Maria J.,Iborra, Sara,Sabater, Maria J.,Vidal, Juan D.
, p. 27 - 38 (2014/06/10)
A bifunctional organocatalyst with ionic liquid properties and with an optimized distance between the acid and basic sites efficiently activates electron deficient olefins for 1,4 conjugated addition, which can be incorporated in different one-pot transformations for the preparation of cyclic and acyclic compounds of biological and synthetic interest. More specifically, the catalyst can be successfully applied for different carbon-carbon (CC) and carbon-heteroatom (C-N, C-O, C-S) bond forming reactions integrated in a cascade sequence. The activity of the organocatalyst has been compared with that of structurally related monofunctional and bifunctional catalysts. The most attractive features of this procedure are the high atom economy and the use of inexpensive starting materials as well as the use of an environmentally friendly catalyst that can be easily recovered due to its ionic liquid properties.
Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes
Wang, Ping-An,Zhang, Dong-Xu,Liu, Xue-Ying
, p. 408 - 419 (2015/01/08)
Using salicylaldehydes and β-nitrostyrenes as starting materials, 2-aryl-3-nitro-2H-chromenes were prepared in good yields (up to 83%) through the combination of 30 mol% of pyrrolidinebenzoic acid catalyzed tandem oxa-Michael-Henry reactions in refluxing
A NOVEL SYNTHESIS OF 6-METHOXY AND 7-METHOXY FLAVONOLS
Rao, Takkellapati Sudhakar,Deshpande, Shubhada,Mathur, Hari Har,Irivedi, Girish Kumar
, p. 1943 - 1946 (2007/10/02)
Condensation of 4-methoxy- (1) or 5-methoxy- (2) salicylaldehyde with ω-nitrostyrene (3-6) in the presence of triethylamine yields 7-methoxy or 6-methoxy-3-nitro-2H-flavene (7-13), which on treatment with alkaline hydrogen peroxide yields the correspondin
