2210-93-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenylpiperazine hydrochloride is used as a chemical intermediate for the preparation of non-peptide oxytocin antagonists, which are important in the development of medications targeting a variety of therapeutic applications, such as the treatment of stress-related disorders and social anxiety. Its acylation properties make it a valuable component in the synthesis process.

InChI:InChI=1/C10H14N2.ClH/c1-2-4-10(5-3-1)12-8-6-11-7-9-12;/h1-5,11H,6-9H2;1H

Upstream product

• 14426-21-2 diethanolamine hydrochloride 
• 137-04-2 2-chloroaniline hydrochloride 
• 22455-79-4 3-(2-anilino-ethyl)-oxazolidin-2-one 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 62-53-3 aniline 
• 77278-63-8 4-phenyl-piperazine-1-carboxylic acid tert-butyl ester 
• 108-86-1 bromobenzene 

Downstream Products

• 253446-34-3 4-phenyl-piperazine-1-carboxylic acid ethyl ester 
• 57498-25-6 N-phenyl-N′-ethylpiperazine 
• 126921-42-4 1-phenyl-4-<β-4-quinolyl>ethyl piperazine 
• 96402-21-0 7,8-Dimethyl-4-(4-phenyl-piperazin-1-ylmethyl)-3,4-dihydro-2H-benzo[b]oxepin-5-one 
• 110164-62-0 N-(2-carbomethoxythien-3-yl)-N'-[2-(4-phenylpiperazin-1-yl)ethyl]urea 
• 110164-69-7 N-(3-carboethoxythien-2-yl)-N'-[2-(4-phenylpiperazin-1-yl)ethyl]urea 
• 95356-06-2 6-<2-(4-phenyl-1-piperazinyl)ethyl>-5,6,7,8-tetrahydro-1,6-naphthyridine 
• 83082-23-9 2-<2-(4-phenyl-1-piperazinyl)ethyl>-1,2,3,4,6,7,8,9-octahydrobenzo<1,6>naphthyridine 
• 98859-10-0 1-phenyl-4-amino>benzoyl>piperazine 
• 103758-51-6 9-[3-(4-phenyl-piperazino)-propyl]-carbazole 
• 201608-45-9 2a-[4-(4-Phenylpiperazinyl)butyl]-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one 
• 562104-64-7 (S)-3-Dibenzylamino-4-(4-phenyl-piperazin-1-yl)-butyronitrile 
• 562104-84-1 (S)-3-Dibenzylamino-4-(4-phenyl-piperazin-1-yl)-butyramide 
• 39819-27-7 1-(2-quinolylmethyl)-4-phenylpiperazine 

Relevant academic research and scientific papers

Design, synthesis and anticancer activity of 5-aryl-4-(4-arylpiperazine-1-carbonyl)-1,2,3-thiadiazoles as microtubule-destabilizing agents

Hereby, we report our efforts on discovery and optimization of a new series of 5-aryl-4-(4-arylpiperazine-1-carbonyl)-1,2,3-thiadiazoles as new microtubule-destabilizing agents along our previous study. Guided by docking model analysis, we introduced the 1,2,3-thiadiazole moiety containing the hydrogen-bond acceptors as B-ring of XRP44X analogues. Extensive structure modifications were performed to investigate the detailed structure and activity relationships (SARs). Some compounds exhibited potent antiproliferative activities against three human cancer cell lines (SGC-7901, A549 and HeLa). The compound 5m exhibited the highest potency against the three cancer cell lines. The tubulin polymerization experiments indicated that compound 5m effectively inhibited the tubulin polymerization, and immunostaining assay revealed that it significantly disrupted microtubule dynamics. Moreover, cell cycle studies revealed that compound 5m dramatically arrested cell cycle progression at G2/M phase.

Design, synthesis and evaluation of antiproliferative and antitubulin activities of 5-methyl-4-aryl-3-(4-arylpiperazine-1-carbonyl)-4H-1,2,4-triazoles

A series of novel 5-methyl-4-aryl-3-(4-arylpiperazine-1-carbonyl)-4H-1,2,4-triazoles possessing 1,2,4-triazole as the hydrogen-bond acceptor were designed, synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them exhibited moderate activities in vitro against the three cancer cell lines including SGC-7901, A549 and HeLa. Compound 6e exhibited the highest potency against the three cancer cell lines. Moreover, the tubulin polymerization experiments indicated that compound 6e could inhibit the tubulin polymerization. Immunofluorescence study and cell cycle analysis clearly revealed compound 6e could disrupt intracellular microtubule organization, arrest cell cycle at the G2/M phase. In addition, molecular docking analysis demonstrated the interaction of compound 6e at the colchicine-binding site of tubulin. These preliminary results suggested that compound 6e is a new colchicine binding site inhibitor and worthy of further investigation.

Design, synthesis and docking study of 4-arylpiperazine carboxamides as monoamine neurotransmitters reuptake inhibitors

Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.

Design, synthesis, and systematic evaluation of 4-arylpiperazine- and 4-benzylpiperidine napthyl ethers as inhibitors of monoamine neurotransmitters reuptake

Two series of 4-arylpiperazine- and 4-benzylpiperidine naphthyl ethers were designed based on structure-activity relationship (SAR) and docking model of reported monoamine neurotransmitters reuptake inhibitors. The compounds were synthesized in 3-simple steps and their biological activities were evaluated. Several compounds were proven to be potent inhibitors of serotonin and norepinephrine reuptake. Computer docking was performed to study the interaction of the most potent compound 35 with human serotonin transporter. The results of the analyses suggest that 4-arylpiperazine- and 4-benzylpiperidine naphthyl ethers might be promising antidepressants worthy of further studies.

Design, synthesis, and biological evaluation of structurally constrained hybrid analogues containing ropinirole moiety as a novel class of potent and selective dopamine D3 receptor ligands

Two series of hybrid analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined (using the method of radioligand binding assay). Compared to comparator agent BP897, compounds 2a and 2c were found to demonstrate a considerable binding affinity and selectivity for D3 receptor, and especially compound 2h was similarly potent and more selective D3R ligand than BP897, a positive reference. Thus, they may provide valuable information for the discovery and development of highly potent dopamine D3 receptor ligands with outstanding selectivity.

Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors

Monoamine transporters regulate the concentration of monoamine neurotransmitters, which are essential for vital physiological processes, and their dysfunction can cause several central nervous system diseases. Monoamine transporters currently appear to be the potential target in the management of these disorders. In this study, homologation and bioisosterism techniques have been used in the designing of new 1,4-disubstituted piperazines and piperidines. These derivatives were synthesized and evaluated as potential triple reuptake inhibitors for studying the structure-activity relationships. The most advanced compound, 1-(4-(5-benzhydryl-1H-tetrazol-1-yl)butyl)-4-(3-phenylpropyl)piperazine (2i), was able to inhibit monoamine neurotransmitter reuptake in an in vitro test (IC50?=?158.7?nM for 5-HT, 99?nM for NE and 97.5?nM for DA). These novel potent triple reuptake inhibitor-based 1,4-disubstituted piperazine and piperidine scaffolds deserve further systematic optimization and pharmacological evaluation.

Indoline-2-ketone D3 receptor ligand and preparation method and application thereof

The invention discloses an indoline-2-ketone D3 receptor ligand, which is a compound as shown in the formula I or pharmaceutical salt thereof, wherein n=2 or 3; R represents H, 4-CH3, 2,3-diCH3, 2-CH3, 4-OCF3, 3-OCH3, 3,4-diCH3 or 4-Cl. In comparison with the prior art, the compound has a strong activity to a dopamine D3 receptor, is used in treating or preventing central nervous and metal diseases such as schizophrenia, Parkinson's disease, drug dependence and relapse, etc., can be used in neuroprotection, and is used as a tool drug for researching D3 receptor structure, function and diseases related to D3 receptor dysfunction.

Design, synthesis, and biological evaluation of arylpiperazine-benzylpiperidines with dual serotonin and norepinephrine reuptake inhibitory activities

The limitations of established serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE) reuptake inhibitors necessitate the development of safer and more effective therapeutic agents. Based on the structures of 4-benzylpiperidine carboxamides and trazodone, arylpiperazine-benzylpiperidines with chemical scaffolds different from those of marketed drugs were designed, synthesized, and evaluated for their neurotransmitter reuptake inhibitory activities. The majority of the synthesized compounds showed greater NE than 5-HT reuptake inhibition. The activities were even greater than those of the standard drug, venlafaxine hydrochloride were. The derivatives with a three-carbon linker showed better activities than the derivatives with a two-carbon linker. Among the newly synthesized compounds, 2d exhibited the strongest reuptake inhibition of the neurotransmitters (IC50 = 0.38 μM for NE and 1.18 μM for 5-HT). The biological activity data demonstrate that arylpiperazine-benzylpiperidines have the potential to be developed as a new class of therapeutic agents to treat neuropsychiatric and neurodegenerative disorders.

Exploration of substituted arylpiperazine–tetrazoles as promising dual norepinephrine and dopamine reuptake inhibitors

In the search for potent dual norepinephrine and dopamine reuptake inhibitors, several substituted arylpiperazine–tetrazoles were designed, synthesized and evaluated for their neurotransmitter reuptake inhibitory activities. Various derivatives exhibited selective and strong neurotransmitter reuptake inhibitory activity. In particular, compounds with a three-carbon linker displayed selective and stronger potency than those with two-carbon and four-carbon linkers. Interestingly, six compounds, 9b, 9c, 9d, 9o, 9q and 9u displayed more effective activity than the standard drug, bupropion. The provided SAR data and potent biological activity can offer useful guidelines for designing dual norepinephrine and dopamine reuptake inhibitors as effective therapeutic agents for treatment of several central nervous system diseases.

Hexahydropyrazine-quinoline D3 receptor ligand and preparation method and use

The present invention discloses a hexahydropyrazino-quinoline D3 receptor ligand, which is a compound shown as formula I or a pharmaceutically acceptable salt thereof, wherein n = 2,3 or 4; R is H, 4-Cl, 2,3-diCl, 4-CH3, 2,3-diCH3, 4-OCF3, 4-OCH3, 2-OCF3, 2,6-di CH3, 3,4-di CH3, 3-CF3, 4-Cl, 3-OCH3, 2-C2H5 or 2-CH3. Compared with the prior art, the compound has strong activity to a dopamine D3 receptor, and can be used for effective treatment of Parkinson's disease, schizophrenia, drug dependence and other central nervous and mental diseases.