57544-16-8

Upstream product

• 101671-01-6 1-nitro-2-(4-chlorophenyl)ethylene 
• 90-02-8 salicylaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 

Downstream Products

• 121824-24-6 (3aS,4R,9bR)-4-(4-Chloro-phenyl)-2-methyl-3a-nitro-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d]isoxazole 
• 1175542-22-9 4-(4-chlorophenyl)-1,4-dihydrochromeno[4,3-d][1,2,3]triazole 
• 1438276-69-7 (6S,6aR,10aR)-7-amino-6,9-bis(4-chlorophenyl)-10-methyl-6a-nitro-6a,10a-dihydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-88-0 (6S,6aR,10aR)-6,9-bis(4-chlorophenyl)-7-imino-10-methyl-6anitro-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-8-carbonitrile 
• 1438276-92-6 (S)-7-amino-6-(4-chlorophenyl)-9-phenyl-6H-benzo[c]chromene-8-carbonitrile 

Relevant academic research and scientific papers

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

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.

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.

Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent

A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.

Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2 H -chromene derivatives as potent anti-breast cancer agents

A series of 2-aryl-3-nitro-2H-chromenes 4a-u were designed as hybrid analogs of flavanone, β-nitrostyrene and nitrovinylstilbene scaffolds. They were synthesized from the reaction of appropriate β-nitrostyrenes and salicylaldehydes in good yields. In vitro cytotoxic activities of compounds 4a-u were tested against breast cancer cell lines including MCF-7, T-47D and MDA-MB-231. Most compounds exhibited good cytotoxic activity against selected cell lines, being more potent than standard drug etoposide. Representatively, 8-methoxy-3-nitro-2-(4-chlorophenyl)-2H-chromene (4l) with IC50 Combining double low line 0.2 μ4M against MCF-7 cells, was 36-times more potent than etoposide. Apoptosis as a mechanism of cell death for selected compounds 4h and 4l was confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis, as well as caspase-3 activation assay.

Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes

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

Catalyst-free 1,3-dipolar cycloaddition of 3-nitrochromen with sodium azide: a facile method for the synthesis of 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives

1,3-Dipolar cycloaddition of 3-nitrochromen with sodium azide under catalyst-free conditions afforded 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives at 80 °C in DMSO is described. The generality of this reaction was demonstrated by synthesiz

3-Nitrochromene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides

The 1,3-dipolar cycloaddition of 2-aryl-3-nitrochromenes with various azomethine ylides has been investigated. The structure and stereochemistry of cycloadducts were studied in detail by NMR spectroscopic methods.

The synthesis of 2,2-disubstituted 3-nitrochromenes from salicylaldehyde and 2,2-disubstituted 1-nitroalkenes

Reactions of salicylaldehyde (1) with β-nitrostyrenes (2), (4), and (6) in the presence of 1,4-diazabicyclo[2.2.2] octane (DABCO) without the use of solvent at 40 °C gave high yields of the corresponding 3-nitrochromenes, respectively. Other conjugated ni

An easy and efficient method for the synthesis of 2,2-dialkyl-3-nitrochromene

Reactions of salicylaldehyde 1, 1,4-diazabicyclo[2.2.2]octane (DABCO), with β-nitrostyrenes 2, 4, 12, 14, and 16, respectively, in the absence of solvent at 40°C gave high yields of 3-nitro-chromenes. Only 96% of trans-3-nitro-4-hydroxyflavans 7 or 98% of 10 were isolated when compounds 6 or 9 reacted with 1 and DABCO under similar conditions. When the reaction temperature was increased to 90°C, 7 and 10 underwent dehydration to generate 74% of 8 and 89% of 11.