174609-74-6

Basic information

• Product Name: 1-(2-CYANOBENZYL)PIPERAZINE
• Synonyms: 1-(2-CYANOBENZYL)PIPERAZINE;2-(PIPERAZIN-1-YLMETHYL)BENZONITRILE;2-(Piperazin-1-ylmethyl)benzonitrile 97%;1-(2-Cyanobenzyl)piperazine, 1-[(2-Cyanophenyl)methyl]piperazine;2-[(Piperazin-1-yl)methyl]benzonitrile97%
• CAS NO: 174609-74-6
• Molecular Formula: C₁₂H₁₅N₃
• Molecular Weight: 201.27
• Mol File: 174609-74-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 334.23 °C at 760 mmHg
• Flash Point: 155.937 °C
• Appearance: /
• Density: 1.133 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 1-(2-CYANOBENZYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CYANOBENZYL)PIPERAZINE(174609-74-6)
• EPA Substance Registry System: 1-(2-CYANOBENZYL)PIPERAZINE(174609-74-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 174609-74-6(Hazardous Substances Data)

Usage

General Description

1-(2-Cyanobenzyl)piperazine is a chemical compound that contains a piperazine ring and a 2-cyanobenzyl group. It is often used in the synthesis of pharmaceuticals and agrochemicals. The piperazine ring is a common structural motif in many pharmaceutical compounds, and its presence in 1-(2-Cyanobenzyl)piperazine suggests that it may have bioactive properties. The 2-cyanobenzyl group is an aromatic compound that contains a nitrile functional group, which can participate in a variety of chemical reactions. Overall, 1-(2-Cyanobenzyl)piperazine is a versatile building block for the synthesis of biologically active compounds.

InChI:InChI=1/C12H15N3/c13-9-11-3-1-2-4-12(11)10-15-7-5-14-6-8-15/h1-4,14H,5-8,10H2

Upstream product

• 110-85-0 piperazine 
• 22115-41-9 2-(bromomethyl)benzonitrile 

Relevant articles and documents

Further SAR studies on natural template based neuroprotective molecules for the treatment of Alzheimer's disease

In our earlier paper, we described ferulic acid (FA) template based novel series of multifunctional cholinesterase (ChE) inhibitors for the management of AD. This report has further extended the structure–activity relationship (SAR) studies of this series of molecules in a calibrated manner to improve upon the ChEs inhibition and antioxidant property to identify the novel potent multifunctional molecules. To investigate the effect of replacement of phenylpiperazine ring with benzylpiperazine, increase in the linker length between FA and substituted phenyl ring, and replacement of indole moiety with tryptamine on this molecular template, three series of novel molecules were developed. All synthesized compounds were tested for their acetyl and butyryl cholinestrases (AChE and BChE) inhibitory properties. Enzyme inhibition and PAS binding studies identified compound 13b as a lead molecule with potent inhibitor property towards AChE/BChE (AChE IC50 = 0.96 ± 0.14 μM, BChE IC50 = 1.23 ± 0.23 μM) compared to earlier identified lead molecule EJMC-G (AChE IC50 = 5.74 ± 0.13 μM, BChE IC50 = 14.05 ± 0.10 μM, respectively). Molecular docking and dynamics studies revealed that 13b fits well into the active sites of AChE and BChE, forming stable and strong interactions with key residues Trp86, Ser125, Glu202, Trp 286, Phe295, Tyr 337 in AChE, and with Trp 82, Gly115, Tyr128, and Ser287 in BChE. The compound, 13b was found to be three times more potent antioxidant in a DPPH assay (IC50 = 20.25 ± 0.26 μM) over the earlier identified EJMC-B (IC50 = 61.98 ± 0.30 μM) and it also was able to chelate iron. Co-treatment of 13b with H2O2, significantly attenuated and reversed H2O2-induced toxicity in the SH-SY5Y cells. The parallel artificial membrane permeability assay-blood brain barrier (PAMPA-BBB) revealed that 13b could cross BBB efficiently. Finally, the in-vivo efficacy of 13b at dose of 10 mg/kg in scopolamine AD model has been demonstrated. The present study strongly suggests that the naturally inspired multifunctional molecule 13b may behave as a potential novel therapeutic agent for AD management.