143468-23-9

Upstream product

• 6959-89-3 2-acetylphenyl 3,4,5-trimethoxybenzoate 
• 1394018-43-9 3-hydroxy-1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 67858-30-4 2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 118-93-4 o-hydroxyacetophenone 
• 127143-42-4 3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2-(3,4,5-trimethoxy-phenyl)-2H-1-benzopyran 
• 143468-41-1 (2S,3R)-3-Chloro-3-nitro-2-(3,4,5-trimethoxy-phenyl)-chroman-4-one 

Downstream Products

• 187585-17-7 3-Amino-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

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.

Synthesis of 2-aryl-3-nitro-4H-1-benzopyran-4-ones

2-Aryl-3-nitro-4H-1-benzopyran-4-ones (or 3-nitroflavones) 3 are conveniently prepared in good yields using a two-step approach starting from 2-aryl-3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2H-1-benzopyrans 1. A general synthesis of the novel 2-aryl-3-chlor