57543-84-7

Usage

InChI:InChI=1/C15H11NO3/c17-16(18)13-10-12-8-4-5-9-14(12)19-15(13)11-6-2-1-3-7-11/h1-10,15H

Upstream product

• 102-96-5 (2-nitroethenyl)benzene 
• 90-02-8 salicylaldehyde 
• 75-52-5 nitromethane 
• 5896-17-3 2-(phenylmethoxy)benzaldehyde 
• 5153-67-3 nitrostyrene 
• 100-52-7 benzaldehyde 

Downstream Products

• 81289-22-7 trans 3-nitro-2-phenyl-3,4-dihydro-2H-<1>benzopyran 
• 81289-22-7 cis 3-nitro-2-phenyl-3,4-dihydro-2H-<1>benzopyran 
• 112513-94-7 2-phenyl-3-hydroxylamino-2H-1-benzopyran 
• 112514-01-9 2-phenyl-3-amino-2H-1-benzopyran 
• 107170-46-7 2-Phenyl-chroman-3-one oxime 
• 113968-76-6 3-nitro-2-phenyl-2H-chromene 
• 81289-44-3 α-(o-hydroxybenzyl)-β-phenylethylamine 
• 81289-32-9 Benzyl-((2R,3S)-2-phenyl-chroman-3-yl)-amine 
• 81289-47-6 Acetic acid 2-(2-nitro-3-phenyl-propyl)-phenyl ester 
• 81289-33-0 ((2R,3S)-2-Phenyl-chroman-3-yl)-(2-pyrrolidin-1-yl-ethyl)-amine 
• 112514-01-9 trans 3-amino-2-phenyl-3,4-dihydro-2H-<1>benzopyran 
• 1175542-14-9 4-phenyl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole 
• 1438276-53-9 (6S,6aR,10aR)-7-amino-10-methyl-6a-nitro-6,9-diphenyl-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-73-3 (6S,6aR,10aR)-7-imino-10-methyl-6a-nitro-6,9-diphenyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 

Relevant 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

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

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

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

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

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

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

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

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

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

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.