883522-59-6

Basic information

• Product Name: 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE
• Synonyms: 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE;4-BROMO-2-NITRO-(4-BENZYL-1-PIPERAZINO)-BENZENE;1-benzyl-4-(4-bromo-2-nitrophenyl)piperazine
• CAS NO: 883522-59-6
• Molecular Formula: C₁₇H₁₈BrN₃O₂
• Molecular Weight: 376.25
• Mol File: 883522-59-6.mol

Chemical Properties

• Boiling Point: 483.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.452±0.06 g/cm3(Predicted)
• PKA: 7.17±0.10(Predicted)
• CAS DataBase Reference: 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE(883522-59-6)
• EPA Substance Registry System: 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE(883522-59-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 883522-59-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE is used as a building block for the synthesis of complex organic molecules, which can be further utilized in the development of new pharmaceutical compounds. Its unique structure and functional groups may contribute to the discovery of novel therapeutic agents with specific biological activities.
Used in Chemical Industry:
In the chemical industry, 3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE is employed as an intermediate in the production of dyes and pigments. The presence of the nitro group suggests that it may exhibit aromatic properties, making it a valuable component in the synthesis of colorants for various applications.
Used in Research and Development:
3-NITRO-4-(4-BENZYL-1-PIPERAZINO)BROMOBENZENE is also used as a compound of interest in research and development. Its molecular structure and properties make it a promising candidate for further study, potentially leading to the discovery of new applications and advancements in the fields of chemistry and materials science.

Upstream product

• 2759-28-6 1-phenylmethylpiperazine 
• 3460-18-2 1,4-dibromo-2-nitrobenzene 

Downstream Products

• 883908-27-8 1-benzyl-4-(2-amino-4-bromo-phenyl)-piperazine 
• 474330-93-3 naphthalene-1-carboxylic acid (5-bromo-2-piperazin-1-yl-phenyl)-amide 
• 883908-06-3 naphthalene-1-carboxylic acid [2-(4-benzyl-piperazin-1-yl)-5-bromo-phenyl]-amide 
• 883908-09-6 2-oxo-2H-chromene-3-carboxylic acid [2-(4-benzyl-piperazin-1-yl)-5-bromo-phenyl]-amide 
• 905575-42-0 naphthalene-1-carboxylic acid (4-piperazin-1-yl-biphenyl-3-yl)-amide 
• 905575-41-9 naphthalene-1-carboxylic acid [4-(4-benzyl-piperazin-1-yl)-biphenyl-3-yl]-amide 
• 905575-45-3 naphthalene-1-carboxylic acid (4-{4-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl]-piperazin-1-yl}-biphenyl-3-yl)-amide 
• 1429199-99-4 N-(2-(4-benzylpiperazin-1-yl)-5-bromophenyl)-2-cyanoacetamide 
• 1429200-03-2 N-(2-(4-Benzylpiperazin-1-yl)-5-bromophenyl)-2-imino-2H-chromene-3-carboxamide 
• 1429200-08-7 N-(2-(4-benzylpiperazin-1-yl)-5-bromophenyl)-2-(phenylimino)-2H-chromene-3-carboxamide 

Relevant articles and documents

Phenylimino-2H-chromen-3-carboxamide derivatives as novel small molecule inhibitors of β-secretase (BACE1)

The inhibition of β secretase (BACE1) is potentially important approach to treatment of Alzheimer disease (AD). A novel series of 4-bromophenyl piperazine derivatives coupled to the phenylimino-2H-chromen-3-carboxamide scaffold were investigated as BACE1 inhibitors in this study. Docking study suggested that the phenyl-imino group of the scaffold establishes favorable π-π stacking interaction with side chain of Phe108 of flap pocket. Some of the docking proposed derivatives were synthesized and evaluated for BACE1 inhibitory activity using a FRET-based assay. High BACE1 inhibitory activities were observed from derivatives containing fused heteroaromtic groups attached through the aliphatic linkage to the N4-piperazine moiety, which may be attributed to the engagement of effective interactions with S1-S′1 sub-pocket residues. Of the most potent compounds, 9e displayed an IC 50 value for BACE1 of 98 nM. Some of these derivatives demonstrated good inhibitory activity on Aβ production in N2a-APPswe cells at 5 and 10 μM. These compounds might be considered as promising BACE1 inhibitory agents that could lower Aβ production in AD.

Naphthyl and coumarinyl biarylpiperazine derivatives as highly potent human β-secretase inhibitors. Design, synthesis, and enzymatic BACE-1 and cell assays

Twenty novel β-secretase inhibitors containing biarylpiperazine moieties belonging to naphthyl and coumarinyl series were designed for their potential use in Alzheimer's disease therapy. Enzymatic and cell-based assays have been carried out. The biological results clearly demonstrate that specific substituents located at the N4-position of the piperazine ring result in excellent in vitro inhibitory potency (IC50 values ranging between 40 and 70 nM), Variable temperature NMR and modeling studies are consistent with the obtained biological data, since these studies confirmed that introduction at the N4-position of the piperazine ring allows productive interactions within the BACE-1 active site, which appear to be determinative for high BACE-1 inhibitory activity. These results are of particular interest since some of the new analogues belonging to the naphthyl series are almost one log more active than the best inhibitor of the similar family recently reported.

BACE-1 inhibitory activities of new substituted phenyl-piperazine coupled to various heterocycles: Chromene, coumarin and quinoline

The protease β-secretase plays a central role in the synthesis of pathogenic amyloid-β in Alzheimer's disease. Here, we report a new series of analogues based on the phenyl-piperazine scaffold coupled to various heterocyclic moieties, which demonstrate improved inhibitory activities on BACE-1 (FRET assay) compared to already known naphthyl counterparts. The obtained results suggest further structural modifications to access to more potent BACE-1 inhibitors.