57543-84-7Relevant academic research and scientific papers
A regio- and stereocontrolled approach to the synthesis of 4-CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2H-chromenes
Kutyashev, Igor B.,Ulitko, Maria V.,Barkov, Alexey Yu.,Zimnitskiy, Nikolay S.,Korotaev, Vladislav Yu.,Sosnovskikh, Vyacheslav Ya.
, p. 18495 - 18504 (2019)
A one-pot three-component reaction of azomethine ylides generated in situ from isatins and sarcosine with 3-nitro-2-(trifluoromethyl)-2H-chromenes in i-PrOH at 55-60 °C leads to the kinetically controlled products-exo-spiro[chromeno[3,4-c]pyrrolidine-3,3′-oxindoles]. When this reaction is carried out in 1,4-dioxane under reflux, the thermodynamically controlled endo-spiro[chromeno[3,4-c]pyrrolidine-1,3′-oxindoles] are preferably formed. The isomerization of the kinetic products in DMSO solution at different temperatures has been studied by NMR spectroscopy and the stepwise mechanism of reversible [3+2] cycloaddition has been confirmed. The cytotoxic activity of some CF3-substituted spiro[chromeno[3,4-c]pyrrolidine-oxindoles] against the HeLa cell line was evaluated by the MTT test.
An expedient synthesis of pyrrolidinyl spirooxindole grafted 3-nitrochromanes through 1,3-dipolar cycloaddition reaction of azomethine ylides
Naga Siva Rao,Raghunathan
, p. 6568 - 6573 (2013)
A facile one-pot synthesis of pyrrolidinyl-spirooxindole grafted 3-nitrochromanes has been accomplished by 1,3-dipolar cycloaddition (1,3-DC) reaction of 3-nitrochromenes with azomethine ylides generated in situ from isatin and secondary amino acids. The
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
The role of L-proline and co-catalysts in the enantioselectivity of oxa-Michael-Henry reactions
do Carmo, Lucas F.,Silva, Simone C.,Machado, Matheus V.,Prata, Paloma S.,Wisniewski, Alberto,Vidal, Diogo M.,Villar, José Augusto F.P.
, p. 893 - 903 (2019/08/27)
The use of L-proline derivatives employed in OXA-Michael-Henry tandem reactions has been an efficient method to produce enantiomerically enriched compounds. In this work it was carried out a study of the OXA-Michael-Henry reactions between salicylaldehyde
Microwave-assisted One-pot, Three-component Regiospecific and Sterospecific Synthesis of Spiro Indanone Pyrrolidine/Piperidine Fused Nitrochromene Derivatives Through 1,3-Dipolar Cycloaddition Reactions
Nayak, Sabita,Panda, Pravati,Mohapatra, Seetaram,Raiguru, Bishnuprasad,Baral, Nilofar
, p. 1757 - 1770 (2019/04/26)
A simple, straightforward, and versatile protocol for the synthesis of spiro indanone pyrrolidine/piperidine fused nitrochromene derivatives is described. The synthesis of a new series of spirocyclic molecules has been expediently accomplished via a one-p
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
Microwave-assisted rapid and efficient synthesis of chromene-fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation
Baral, Nilofar,Kumar, P. Sudhir,Mishra, Deepak Ranjan,Mishra, Nilima Priyadarsini,Mohapatra, Seetaram,Nayak, Mukesh,Nayak, Sabita,Panda, Pravati,Raiguru, Bishnu Prasad
, (2020/01/03)
The current study aimed to identify a new strategy of FeCl3 catalyzed multicomponent synthesis of substituted 2H-chromene–fused pyrrole derivatives. A series of chromene-based pyrrole prepared by employing an array of 3-nitro-2H-chromenes, anil
Molecular diversity of the domino annulation reaction of 2-aryl-3-nitrochromenes with pivaloylacetonitriles
Jiang, Wang,Sun, Jing,Liu, Ru-Zhang,Yan, Chao-Guo
supporting information, p. 5816 - 5822 (2018/08/21)
In the presence of triethylamine, the domino annulation reaction of two molecules of pivaloylacetonitrile with one molecule of 2-aryl-3-nitrochromene in tetrahydrofuran resulted in the unprecedented imino-substituted dihydrofuro[2,3-c]chromene derivatives in high yields. More importantly, the above domino reaction in refluxing methanol or ethanol afforded alkoxy-substituted chromeno[3,4-b]pyridines in satisfactory yields. However, a similar reaction of benzoylacetonitrile with 2-aryl-3-nitrochromenes in basic medium gave the expected furo[2,3-c]chromene derivatives in moderate yields.
Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis
Vroemans, Robby,Verhaegen, Yenthel,Dieu, My Tran Thi,Dehaen, Wim
supporting information, p. 2689 - 2697 (2018/11/03)
A new metal-free one-pot three-component procedure towards fully substituted triazolochromenes has been developed, starting from commercially available materials. Salicylaldehydes and nitroalkenes were reacted under solvent-free conditions, followed by a
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.
