651733-07-2

Basic information

• Product Name: N-(2-(BROMOMETHYL)-5-NITROPHENYL)ACETAMIDE
• Synonyms: N-(2-(BROMOMETHYL)-5-NITROPHENYL)ACETAMIDE
• CAS NO: 651733-07-2
• Molecular Formula: C₉H₉BrN₂O₃
• Molecular Weight: 273.08
• Mol File: 651733-07-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-(BROMOMETHYL)-5-NITROPHENYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-(BROMOMETHYL)-5-NITROPHENYL)ACETAMIDE(651733-07-2)
• EPA Substance Registry System: N-(2-(BROMOMETHYL)-5-NITROPHENYL)ACETAMIDE(651733-07-2)

Safety Data

• Hazardous Substances Data: 651733-07-2(Hazardous Substances Data)

Upstream product

• 99-55-8 2-methyl-5-nitroaniline 
• 2879-79-0 N-(2-methyl-5-nitrophenyl)acetamide 

Downstream Products

• 78468-34-5 (2-Amino-4-nitrophenyl)methan-1-ol 
• 651733-13-0 2-acetamido-4-nitrobenzyl alcohol 
• 651733-08-3 2-acetamido-4-nitro-α-phthalimido toluene 

Relevant articles and documents

Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation

The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: Synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 °C and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 °C. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy.

Nitroaryl Phosphoramides as Novel Prodrugs for E. coli Nitroreductase Activation in Enzyme Prodrug Therapy

Cyclic and acyclic nitroaryl phosphoramide mustard analogues were activated by E. coli nitroreductase, an enzyme explored in GDEPT. The more active acyclic 4-nitrobenzyl phosphoramide mustard (7) showed 167 500x selective cytotoxicity toward nitroreductase-expressing V79 cells with an IC50 as low as 0.4 nM. This is about 100x more active and 27x more selective than CB1954 (1). The superior activity was attributed to its better substrate activity (kcat/Km 19x better than 1) and/or excellent cytotoxicity of phosphoramide mustard released.