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Usage

Uses

Used in Pharmaceutical Development:
1-(4-Bromobenzyl)piperazine is used as a precursor in the synthesis of drugs for targeting central nervous system receptors, such as dopamine and serotonin receptors, due to its piperazine moiety and benzyl group with a bromine atom. This makes it a valuable compound in the development of medications for treating neurological and psychiatric disorders.
Used in Medicinal Chemistry Research:
1-(4-Bromobenzyl)piperazine is utilized as a research tool in medicinal chemistry to explore the effects of structural modifications on receptor binding and drug efficacy. Its unique combination of functional groups allows for the investigation of structure-activity relationships and the optimization of drug candidates.
Used in Drug Design and Optimization:
1-(4-Bromobenzyl)piperazine is employed as a key component in the design and optimization of new drugs. The bromine atom in the benzyl group can be used for further functionalization, providing a versatile platform for the attachment of various functional groups to enhance the compound's pharmacological properties.
Used in Radioligand Synthesis:
1-(4-Bromobenzyl)piperazine can be used as a starting material for the synthesis of radiolabeled ligands for receptor binding studies. The incorporation of radioactive isotopes, such as iodine-125 or carbon-14, allows for the tracking of the compound's interaction with target receptors, providing valuable insights into receptor binding kinetics and mechanisms.
Used in Drug Screening Assays:
1-(4-Bromobenzyl)piperazine is utilized in high-throughput screening assays to identify potential drug candidates with desired pharmacological properties. Its presence in these assays helps in the rapid evaluation of compound libraries for their ability to modulate receptor activity and other biological targets.

InChI:InChI=1/C11H15BrN2/c12-11-3-1-10(2-4-11)9-14-7-5-13-6-8-14/h1-4,13H,5-9H2

Upstream product

• 110-85-0 piperazine 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 844891-10-7 tert-butyl 4-[(4-bromophenyl)methyl]piperazine-1-carboxylate 
• 589-17-3 p-bromobenzyl chloride 
• 106-38-7 para-bromotoluene 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 

Downstream Products

• 368879-17-8 4-[(4-methylpiperazin-1-yl)methyl]bromobenzene 
• 100141-14-8 4-(4-bromo-benzyl)-piperazine-1-carboxylic acid amide 
• 1218949-50-8 2-[(4-bromobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]ethanone 
• 1383276-04-7 C₂₀H₂₃BrN₂O 
• 1398718-03-0 (S)-1-amino-N-(1-cyano-2-(4'-((4-(oxazol-2-ylmethyl)piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide 
• 1398718-72-3 PZ₁₀₅₇-2 
• 1398718-70-1 C₁₅H₁₈BrN₃O 
• 1403353-37-6 C₁₈H₁₈BrN₅O 
• 1421322-11-3 C₂₉H₂₈BrClN₆O 

Relevant academic research and scientific papers

SYNTHESIS, CRYSTAL STRUCTURE, AND BIOLOGICAL EVALUATION OF (E)-1-(4-(4-BROMOBENZYL)PIPERAZIN-1-YL)- 3-(4-CHLOROPHENYL)PROP-2-EN-1-ONE

Abstract: Title compound (E)-1-(4-(4-bromobenzyl)piperazin-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one (5) (C20H20BrClN2O, Mr?=?419.74) is designed, synthesized, and evaluated for its biological activity. Its structure is confirmed by FTIR, 1H and 13C NMR, HRMS, and X-ray single crystal diffraction. The structure is stabilized via inter- as well as intra- C–H…O interactions and intra hydrogen bonding C–H…N interactions. The Hirshfeld surface intermolecular interactions are studied using the crystal structure. The maximum surface area of the molecule is occupied by C–H…O interactions. In addition, the biological activity in vitro and in vivo of title compound 5 is also evaluated.

New potent antifungal triazole alcohols containing N-benzylpiperazine carbodithioate moiety: Synthesis, in vitro evaluation and in silico study

A number of 1H-1,2,4-triazole alcohols containing N-(halobenzyl)piperazine carbodithioate moiety have been designed and synthesized as potent antifungal agents. In vitro bioassays against different Candida species including C. albicans, C. glabrata, C. parapsilosis, C. krusei, and C. tropicalis revealed that the N-(4-chlorobenzyl) derivative (6b) with MIC values of 0.063–0.5 μg/mL had the best profile of activity, being 4–32 times more potent than fluconazole. Docking simulation studies confirmed the better fitting of compound 6b in the active site of lanosterol 14α-demethylase (CYP51) enzyme, the main target of azole antifungals. Particularly, the potential of compound 6b against fluconazole-resistant isolates along with its minimal toxicity against human erythrocytes and HepG2 cells make this prototype compound as a good lead for discovery of potent and safe antifungal agents.

Design, synthesis and neuroprotective activities of novel cinnamide derivatives containing benzylpiperazine moiety

A new series of cinnamide derivatives 6a–l were synthesized by the reaction of acyl chlorides with various substituted benzylpiperazines. The structures were characterized by 1H NMR, 13C NMR, and HRMS. The potential neuroprotective activities of cinnamide analogs were evaluated in differentiated rat pheochromocytoma cells (PC12 cells) and in mice subjected to acute cerebral ischemia. Among the series, 6a, 6b, and 6c, featuring a 1,3-benzodioxole moiety, showed potent neuroprotection both in vivo and in vitro. The three compounds were selected and further studied to determine their mechanism of action. MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 6a, 6b, and 6c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke.

Design, Synthesis, and Cytotoxic Evaluation of Certain 7-Chloro-4-(piperazin-1-yl)quinoline Derivatives as VEGFR-II Inhibitors

Signaling pathway inhibition of VEGFR-II is visualized as valuable tool in cancer management. In the current study, the synthesis of novel 1-4-(7-chloroquinolin-4-yl)piperazin-1-yl)-2-(N-substituted-amino)-ethanone derivatives (4a–t) was achieved through the amination of 2-chloro-1-(4-(7-chloroquinolin-4-yl)piperazin-1-yl)ethanone (3) with different secondary amines. The structures of the target compounds were confirmed by IR, 1H-NMR, 13C-NMR, HRMS, and microanalysis. Compounds 4a–t were subjected to in vitro anticancer screening against human breast cancer (MCF-7) and prostate cancer (PC3) cell lines. The highest cytotoxicty against both cell lines was displayed by 2-(4-(4-bromobenzyl)piperazin-1-yl)-1-(4-(7-chloroquinolin-4-yl)piperazin-1-yl)ethanone (4q), with IC50 values of 6.502 and 11.751 μM against MCF-7 and PC3 cells, respectively, compared with the standard drug doxorubicin (MCF-7: 6.774 μM, PC3: 7.7316 μM). Due to its notable activity toward MCF-7 cells, 4q was further evaluated as VEGFR-II inhibitor, showing an IC50 of 1.38 μM compared to sorafenib (0.33 μM). The docking study proved that 4q has a binding mode akin to that of VEGFR-II inhibitors.

Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands

This study presents the synthesis and biological evaluation of a new series of arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as sigma receptor ligands. It was found that a number of halogen substituted sulfonamides display relatively high and low affinities to σ1 and σ2 receptors, respectively. The σ1 affinities and subtype selectivities of four piperidine derivatives were also found to be generally comparable to those of piperazine analogues. Compared to σ1-Rs compounds with n = 0 and 2, those with n = 1 proved to have optimal length of carbon chain by exhibiting higher affinities. Within this series, the 4-benzyl-1-(3-iodobenzylsulfonyl)piperidine sigma ligand was identified with 96-fold σ1/σ2 selectivity ratio (Kiσ1 = 0.96 ± 0.05 nM and K iσ2 = 91.8 ± 8.1 nM).

PROCASPASE-ACTIVATING COMPOUNDS AND COMPOSITIONS

The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the compounds and compositions, including the use of compounds and compositions in therapy for the treatment of cancer and selective induction of apoptosis in cells.

PEPTIDYL NITRILCOMPOUNDS AS PEPTIDASE INHIBITORS

The invention relates to compounds of Formula (II) and their use in theraphy as peptidase inhibitors.

Synthesis and pharmacological evaluation of 2,4-dinitroaryldithiocarbamate derivatives as novel monoacylglycerol lipase inhibitors

Monoacylglycerol lipase (MAGL) is responsible for signal termination of 2-arachidonoylglycerol (2-AG), an endocannabinoid neurotransmitter endowed with several physiological effects. Previously, we showed that the arylthioamide scaffold represents a privileged template for designing MAGL inhibitors. A series of 37 compounds resulting from pharmacomodulations around the arylthioamide template were synthesized and tested to evaluate their inhibitory potential on MAGL activity as well as their selectivity over fatty acid amide hydrolase (FAAH), another endocannabinoid-hydrolyzing enzyme. We have identified 2,4-dinitroaryldithiocarbamate derivatives as a novel class of MAGL inhibitors. Among the synthesized compounds, we identified [2,4-dinitrophenyl-4-(4-tert- butylbenzyl)piperazine-1-carbodithioate] (CK37), as the most potent MAGL inhibitor within this series (IC50 = 154 nM). We have also identified [2,4-dinitrophenyl-4-benzhydrylpiperazine-1-carbodithioate] (CK16) as a selective MAGL inhibitor. These compounds are irreversible MAGL inhibitors that probably act by interacting with Cys208 or Cys242 and Ser122 residues of the enzyme. Moreover, CK37 is able to raise 2-arachidonoylglycerol (2-AG) levels in intact cells.

Gas-phase nucleophilic aromatic substitution between piperazine and halobenzyl cations: Reactivity of the methylene arenium form of benzyl cations

Methylene arenium involved in SNAr: The gas-phase nucleophilic aromatic substitution reactions of halobenzyl cations with piperazine through a cationic σ complex were studied using ESI mass spectrometry. This study demonstrates that the methylene arenium form of halobenzyl cations exhibits nucleophilic substitution reactivity at the phenyl ring (see scheme). Copyright

INHIBITORS OF STEAROYL-COA DESATURASE

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.