81289-17-0

Upstream product

• 4230-93-7 3,4-dimethoxynitrostyrene 
• 90-02-8 salicylaldehyde 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 81289-38-5 2-[3-(3,4-Dimethoxy-phenyl)-2-nitro-propyl]-phenol 
• 81289-24-9 (2R,3S)-2-(3,4-Dimethoxy-phenyl)-3-nitro-chroman 
• 81289-24-9 (2R,3R)-2-(3,4-Dimethoxy-phenyl)-3-nitro-chroman 
• 105849-80-7 2-(3,4-Dimethoxy-phenyl)-chroman-3-one 
• 6889-80-1 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 
• 81289-46-5 2-[2-Amino-3-(3,4-dimethoxy-phenyl)-propyl]-phenol 

Relevant academic research and scientific papers

A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles

The synthesis of several 4-aryl-1,4-dihydrochromene-triazoles was achieved via a metal-free "one-pot"procedure using PEG400 as the sole solvent in an eco-friendly process. Using microwave irradiation, the triazole derivatives were obtained in good yields and short reaction times starting from readily accessible building blocks.

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.

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.

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.

Synthesis of 2-Aryl-3-nitrochromenes

2-Aryl-3-nitrochromenes have been prepared by condensing salicylaldehyde with β-nitrostyrenes (III) in the presence of triethylamine.

Sodium Borohydride Reduction of 3-Nitro-2-substituted-phenyl-2H-benzopyrans

Reaction of 3-nitro-2-substituted-phenyl-2H-benzopyrans (1-8) with NaBH4 at 5-10 deg C followed by reduction of the nitro group with hydrazine hydrate in the presence of Raney-nickel furnishes 3-amino-2-substituted-phenyl-3,4-dihydro-2H-benzopyrans