86945-25-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-Aminoethyl)-1-benzylpiperidine is used as a drug candidate for its psychoactive effects, with potential applications in the development of medications targeting various medical conditions. Its pharmacological properties are currently under investigation to determine its efficacy and safety in clinical settings.
Used in Research and Development:
In the field of scientific research, 4-(2-Aminoethyl)-1-benzylpiperidine serves as a valuable compound for studying the effects of psychoactive substances on the human body. It contributes to the advancement of knowledge in pharmacology and may lead to the discovery of new therapeutic agents.

InChI:InChI=1/C14H22N2/c15-9-6-13-7-10-16(11-8-13)12-14-4-2-1-3-5-14/h1-5,13H,6-12,15H2

Upstream product

• 86945-27-9 1-benzyl-4-cyanomethylpiperidine-4-carbonitrile 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 1463-52-1 ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate 
• 194612-36-7 1-benzyl-4-(2-chloroethyl)piperidine 
• 202002-66-2 2-(piperidin-4-yl)acetonitrile 
• 256411-39-9 tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate 
• 197569-11-2 4-(cyanomethylidene)piperidine-1-carboxylic acid tert-butyl ester 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 100-39-0 benzyl bromide 
• 55022-82-7 2-(1-benzylpiperidin-4-ylidene)acetonitrile 
• 616897-44-0 2-(1-benzylpiperidin-4-ylidene)malononitrile 

Downstream Products

• 113027-62-6 N-(2-(1-benzylpiperidin-4-yl)ethyl)nicotinamide 
• 126848-98-4 N-(2-(1-benzylpiperidin-4-yl)ethyl)isonicotinamide 
• 144319-70-0 1-benzyl-4-<2-(N-formylamino)ethyl>piperidine 
• 126848-93-9 4-Acetyl-N-[2-(1-benzyl-piperidin-4-yl)-ethyl]-benzamide 
• 126848-94-0 1-benzyl-4-<2-amino>ethyl>piperidine 
• 145232-89-9 1-(3,4-methylenedioxybenzoyl)-3-[2-(1-benzyl-4-piperidyl)ethyl]thiourea 

Relevant academic research and scientific papers

Claulansine F-donepezil hybrids as anti-alzheimer’s disease agents with cholinergic, free-radical scavenging, and neuroprotective activities

The multifactorial nature of Alzheimer’s disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A total of 26 Claulansine F-donepezil hybrids were designed and synthesized as multitarget drugs. Among these compounds, six compounds exhibited excellent acetylcholinesterase (AChE) inhibitory activity (half maximal inhibitory concentration (IC50) 1.63-4.62 μM). Moreover, (E)-3-(8-(tert-Butyl)-3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazol- 5-yl)-N-((1-(2-chlorobenzyl)piperidin-4-yl)methyl)acrylamide (6bd) exhibited better neuroprotective effects against OGD/R (oxygen-glucose deprivation/reoxygenation) than lead compound Claulansine F. Furthermore, 6bd could cross the blood-brain barrier in vitro. More importantly, compared to edaravone, 6bd had stronger free-radical scavenging activity. Molecular docking studies revealed that 6bd could interact with the catalytic active site of AChE. All of these outstanding in vitro results indicate 6bd as a leading structure worthy of further investigation.

Structure-activity relationship study of tryptophan-based butyrylcholinesterase inhibitors

A series of tryptophan-based selective nanomolar butyrylcholinesterase (BChE) inhibitors was designed and synthesized. Compounds were optimized in terms of potency, selectivity, and synthetic accessibility. The crystal structure of the inhibitor 18 in complex with BChE revealed the molecular basis for its low nanomolar inhibition (IC50 = 2.8 nM). The favourable in vitro results enabled a first-in-animal in vivo efficacy and safety trial, which demonstrated a positive impact on fear-motivated and spatial long-term memory retrieval without any concomitant adverse motor effects. Altogether, this research culminated in a handful of new lead compounds with promising potential for symptomatic treatment of patients with Alzheimer's disease.

Rational Design and Multibiological Profiling of Novel Donepezil-Trolox Hybrids against Alzheimer's Disease, with Cholinergic, Antioxidant, Neuroprotective, and Cognition Enhancing Properties

A novel series of donepezil-trolox hybrids were designed, synthesized, and evaluated as multifunctional ligands against Alzheimer's disease (AD). Biological assays showed that these derivatives possessed moderate to good inhibitory activities against acetylcholinesterase (AChE) and monoamine oxidase B (MAO-B) as well as remarkable antioxidant effects. The optimal compound 6d exhibited balanced functions with good inhibition against hAChE (IC50 = 0.54 μM) and hMAO-B (IC50 = 4.3 μM), significant antioxidant activity (41.33 μM IC50 by DPPH method, 1.72 and 1.79 trolox equivalent by ABTS and ORAC methods), excellent copper chelation, and Aβ1-42 aggregation inhibition effect. Furthermore, cellular tests indicated that 6d has very low toxicity and is capable of combating oxidative toxin (H2O2, rotenone, and oligomycin-A) induced neurotoxicity. Most importantly, oral administration of 6d demonstrated notable improvements on cognition and spatial memory against scopolamine-induced acute memory deficit as well as d-galactose (d-gal) and AlCl3 induced chronic oxidative stress in a mouse model without acute toxicity and hepatotoxicity. In summary, both in vitro and in vivo results suggested that 6d is a valuable candidate for the development of a safe and effective anti-Alzheimer's drug.

Cyclamine alkylamide ferulate compound as well as preparation method and application thereof

The invention belongs to the technical field of organic synthesis and particularly relates to a cyclamine alkylamide ferulate compound as well as a preparation method and application thereof. The preparation method comprises the following steps: enabling potassium phthalimide serving as a start raw material to react with 1-substituted-4-haloalkyl piperidine under the effects of a solvent and alkali to obtain a phthalimide alkylamine compound; performing hydrazinolysis of the phthalimide alkylamine compound and hydrazine hydrate to obtain a primary amine compound; and adding ferulic acid, a condensing agent and a solvent into the primary amine compound for a condensation reaction to obtain a product of cyclamine alkylamide ferulate compound. The cyclamine alkylamide ferulate compound provided by the invention is of a simple chemical structure, the chemical reactions in the preparation process are thorough, the product yield is high, the operation is convenient, the cost is low, and the product can be used for perfectly treating the neurodegenerative diseases.

Synthesis and evaluation of multi-target-directed ligands against Alzheimer's disease based on the fusion of donepezil and ebselen

A novel series of compounds obtained by fusing the cholinesterase inhibitor donepezil and the antioxidant ebselen were designed as multi-target-directed ligands against Alzheimer's disease. An in vitro assay showed that some of these molecules did not exhibit highly potent cholinesterase inhibitory activity but did have various other ebselen-related pharmacological effects. Among the molecules, compound 7d, one of the most potent acetylcholinesterase inhibitors (IC50 values of 0.042 μM for Electrophorus electricus acetylcholinesterase and 0.097 μM for human acetylcholinesterase), was found to be a strong butyrylcholinesterase inhibitor (IC50 = 1.586 μM), to possess rapid H2O2 and peroxynitrite scavenging activity and glutathione peroxidase-like activity (ν0 = 123.5 μM min-1), and to be a substrate of mammalian TrxR. A toxicity test in mice showed no acute toxicity at doses of up to 2000 mg/kg. According to an in vitro blood-brain barrier model, 7d is able to penetrate the central nervous system.

Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

Abstract Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study.

Synthesis of 1-benzyl-4-[2-(3-thienylcarbonylamino)ethyl]piperidine as a novel potential cholinesterase inhibitor

Potentiating of cholinergic activity which increases the acetylcholine level in the brain has been regarded as an approach for the palliative treatment of alzheimer's disease. Accordingly, inhibition of the acetyl cholinesterase enzyme is considered to be a viable and attractive therapeutic strategy for alzheimer's disease patients. In an attempt to find a new acetyl cholinesterase inhibitor (AChEI), 1-benzylpiperidin- 4-yl-ethylamine has been reacted with thiophen-3-carbonylchloride to prepare 1-benzyl-4-[2-(3-thienylcarbonyl-amino) ethyl]piperidine, as potential acetyl cholinesterase inhibitor. The structure of target compound was confirmed by mass, NMR and IR spectra.

Synthesis and evaluation of tacrine-E2020 hybrids as acetylcholinesterase inhibitors for the treatment of Alzheimer's disease

Tacrine-E2020 hybrids and some related compounds were prepared and their bioactivities on the Alzheimer's Disease were assayed. The optimum hybrid inhibitor 3 is much more potent and selective than tacrine in vitro. Tacrine-E2020 hybrids and some related compounds were prepared and their bioactivities on the Alzheimer's disease were assayed. The optimum hybrid inhibitor 3 is 37-fold more potent and 31-fold more selective than tacrine in vitro.

Benzopiperidine derivatives

Benzopiperidine derivatives represented by formula (I), salts thereof or hydrates thereof, processes for producing the same and drugs comprising the same: wherein the variables are as described in the specification. These compounds are useful as drugs efficacious in the prevention and treatment of these various inflammatory diseases and immunologic diseases, such as rheumatoid arthritis, atopic dermatitis, psoriasis, asthma, and rejection reaction accompanying organ transplantation.

Aminopyridazines as acetylcholinesterase inhibitors

Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 μM on homogenized rat striatum AChE), a series of 3-amino-6- phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high AChE inhibition are as follows: (i) presence of a central pyridazine ring, (ii) necessity of a lipophilic cationic head, (iii) change from a 2- to a 4-5-carbon units distance between the pyridazine ring and the cationic head. Among all the derivatives investigated, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6- phenylpyridazine (3y), which shows an IC50 of 0.12 μM on purified AChE (electric eel), was found to be one of the most potent anti-AChE inhibitors, representing a 5000-fold increase in potency compared to minaprine.