56056-37-2

Usage

Chemical structure

Contains a benzyl-piperazine group and a chloro-ethanone group.

Application

Often used in pharmaceutical research as a building block for the synthesis of various compounds.

Pharmacological potential

Presence of the benzyl-piperazine group suggests it may have potential pharmacological activity.

Reactivity

The chloro-ethanone group can be reactive in organic synthesis.

Use in drug development

Could be used in the development of new drugs.

Research tool

Can be used as a research tool in the study of biological systems.

Safety precautions

Important to handle 1-(4-BENZYL-PIPERAZIN-1-YL)-2-CHLORO-ETHANONE with care due to potential health hazards if not used properly.

Upstream product

• 2759-28-6 1-phenylmethylpiperazine 
• 79-04-9 chloroacetyl chloride 
• 100-44-7 benzyl chloride 
• 57260-70-5 4-benzyl-piperazine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 349423-62-7 2-{2-[4-benzylpiperazin-1-yl]-2-oxoethyl}isoindoline-1,3-dione 
• 116876-81-4 1-Benzyl-4-(3,4,5-trimethoxyphenoxyacetyl)piperazine 
• 1289155-05-0 (S)-1-(4-benzylpiperazin-1-yl)-2-((1-(benzylsulfonyl)pyrrolidin-3-yl)amino)ethanone 
• 361979-30-8 2-amino-1-(4-benzylpiperazin-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Indoles and 1-(3-(benzyloxy)benzyl)piperazines: Reversible and selective monoamine oxidase B inhibitors identified by screening an in-house compound library

The therapeutic indications for monoamine oxidases A and B (MAO-A and MAO-B) inhibitors that have emerged from biological studies on animal and cellular models of neurological and oncological diseases have focused drug discovery projects upon identifying

Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity

ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.

Propionamide Derivatives as Dual μ-Opioid Receptor Agonists and σ1Receptor Antagonists for the Treatment of Pain

A new series of propionamide derivatives was developed as dual μ-opioid receptor agonists and σ1receptor antagonists. Modification of a high-throughput screening hit originated a series of piperazinylcycloalkylmethyl propionamides, which were e

Design and synthesis of C-19 isosteviol derivatives as potent and highly selective antiproliferative agents

Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. M

Chloroquinoline-acetamide hybrids: A promising series of potential antiprotozoal agents

In an endeavour to develop efficacious antiprotozoal agents 2-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]acetamide derivatives were synthesized and screened in vitro against the HM1:IMSS strain of E. histolytica and 3D7 strain of P. falciparum. Among the twenty-seven synthesized compounds, eleven evinced propitious anti-amoebic activity with IC50 values ranging from 0.41 to 1.80 μM) lower than the standard drug metronidazole (IC50 1.80 μM). All the compounds inhibited the in vitro growth of P. falciparum (IC50 range: 0.30-33.52 μM). Compounds A22 and A25 were found to be the most active antimalarial derivatives, and compound A16 the most active in inhibiting β-haematin formation; however compound A25 displayed the more favourable safety profile. The crystal structure for the compounds A7, A8, A12 and A21 was also determined. The molecular docking of crystal resolved inhibitors with PfDHFR allowed identification of stabilizing interactions within enzyme active sites. These compounds affirm the potential for further derivatives to enhance antiprotozoal activity whilst retaining their safety profile.

Exploration of (S)-3-aminopyrrolidine as a potentially interesting scaffold for discovery of novel Abl and PI3K dual inhibitors

Based on the literature-reported compensatory effect of PI3K on Abl inhibition and the improved preclinical effect of drug combination of Abl and PI3K inhibitors, a series of compounds bearing novel scaffold of (S)-3-aminopyrrolidine was identified as Abl and PI3K dual inhibitors through support vector machine screening tool, which were subsequently synthesized and tested. Most compounds demonstrated promising cytoxicity against a CML leukemia cell-line K562 and moderate inhibition against Abl and PI3K kinases. These compounds induced no apoptosis in K562 cell-line, suggesting that their cytotoxic activities are unlikely duo to other known anti-CML mechanisms. Molecular docking study further showed that the compound 5k could bind with both Abl and PI3K, but the weaker binding with Abl compared to Imatinib is consistent with its low kinase inhibitory rates. These plus literature-reported evidences suggest that the promising cytotoxic effect of our novel compounds might be due to the collective effect of Abl and PI3K inhibition.

Design, synthesis, and structure-activity relationships of a series of 3-[2-(1-benzylpiperidin-4-yl)ethylamino]pyridazine derivatives as acetylcholinesterase inhibitors

Starting from the 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6-phenylpyridazine 1, we performed the design, the synthesis, and the structure-activity relationships of a series of pyridazine analogues acting as AChE inhibitors. Structural modifications were achieved on four different parts of compound 1 and led to the following observations: (i) introduction of a lipophilic environment in the C-5 position of the pyridazine ring is favorable for the AChE-inhibitory activity and the AChE/BuChE selectivity; (ii) substitution and various replacements of the C-6 phenyl group are possible and led to equivalent or slightly more active derivatives; (iii) isosteric replacements or modifications of the benzylpiperidine moiety are detrimental to the activity. Among all derivatives prepared, the indenopyridazine derivative 4g was found to be the more potent inhibitor with an IC50 of 10 nM on electric eel AChE. Compared to compound 1, this represents a 12-fold increase in potency. Moreover, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-5-methyl-6-phenylpyridazine 4c, which showed an IC50 of 21 nM, is 100-times more selective for human AChE (human BuChE/AChE ratio of 24) than the reference compound tacrine.

Pyridazinone derivatives with pharmaceutical activity

A 3(2H)-pyridazinone derivative of the formula (I) its salt, a process for its production and a pharmaceutical composition containing it. STR1 wherein each of R1, R2 and R3 which are independent of one another, is a hydrogen atom or a C1-4 alkyl group, X is a chlorine atom or a bromine atom, Y1 is a hydrogen atom, a halogen atom, a nitro group, an amino group or a C1-4 alkoxy group, Y2 is a hydrogen atom, a halogen atom, a hydroxyl group, a C1-4 alkyl group or a C1-4 alkoxy group, A is a C1-5 alkylene chain which may be substituted by a hydroxyl group, B is a carbonyl group or a methylene chain which may be substituted by a C1-4 alkyl group, and each of R4 and R5 which are independent of each other, is a C1-4 alkyl group, or R4 is a hydrogen atom and R5 is --Z--Ar (wherein Z is a C1-5 alkylene chain, and Ar is an aromatic 6-membered ring which may contain a nitrogen atom), or R4 and R5 together form a C2-6 cyclic alkylene group, or R4 and R5 form together with the adjacent nitrogen atom a 4-substituted piperazine ring of the formula: STR2 wherein R6 is a C1-4 alkyl group.

Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents

Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (±)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-p