49678-57-1

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 108-03-2 1-Nitropropane 

Downstream Products

• 78303-42-1 4-(4-Chloro-phenyl)-hept-6-en-3-one 
• 36263-13-5 4-p-chlorophenyl-5-ethyl-3-phenyl-2-pyrrolidinone 
• 145028-36-0 [1-(4-Chloro-phenyl)-2-oxo-butyl]-phosphonic acid diethyl ester 

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.

Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines

A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines 1 from available 5,6-dihydro-4H-1,2-oxazine N-oxides 2 has been described. The key step of the process-the rearrangement of 3-alkiliden-2-siloxy-tetrahydro-1,2-oxazines 3 (ASENA)-was thoroughly investigated. Optimal experimental conditions were developed. A possible pathway of the ASENA rearrangement was proposed.

Supported organic catalysts: Synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes over propylamine supported on MCM-41 silica as a reusable catalyst

MCM-41-supported propylamine showed high catalytic efficiency in the nitroaldol condensation between nitroalkanes and aromatic aldehydes.

Zeolite as base catalyst: Nitroaldolic condensation

The use of heterogeneous catalysts in producing petrochemicals and fine chemicals is one of the most successful lines in catalysis research. They may replace dangerous, corrosive, or toxic catalysts in some cases. The use of zeolites as main catalysts in petrochemical cracking reactions and in oil processing is a case of specific importance. The activity and selectivity of alkaline Y and X zeolites in promoting the nitroaldolic condensation of aromatic aldehydes with nitroalkanes affording nitroalkenes were studied. The reaction was promoted by the intrinsic basicity of the zeolites that increased with increases in both the aluminum content in the framework and the radius of the counter cation. The zeolite cages were microreactors, the walls of which were the basic sites whose number and strength could be controlled by choosing the chemical composition. The activity of substituted benzaldehyde revealed the influence of electronic effects. Steric factors played a critical role regarding the nitroalkanes; the combined effect of shape selectivity and basicity had to be considered in the heterogeneous nitroaldolic condensation.