81289-18-1

Upstream product

• 2982-55-0 1-benzyloxy-4-(2-nitroethenyl)benzene 
• 90-02-8 salicylaldehyde 
• 17354-63-1 4-(2-nitro-propenyl)-anisole 
• 2982-55-0 (E)-1-(benzyloxy)-4-(2-nitrovinyl)benzene 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 81289-37-4 2-[3-(4-Benzyloxy-phenyl)-2-nitro-propyl]-phenol 
• 81289-23-8 (2R,3S)-2-(4-Benzyloxy-phenyl)-3-nitro-chroman 
• 81289-23-8 (2R,3R)-2-(4-Benzyloxy-phenyl)-3-nitro-chroman 
• 81289-28-3 (2S,3R)-2-(4-Benzyloxy-phenyl)-chroman-3-ylamine 
• 81289-48-7 Acetic acid 2-[3-(4-benzyloxy-phenyl)-2-nitro-propyl]-phenyl ester 
• 81289-45-4 2-[2-Amino-3-(4-benzyloxy-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.

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