55022-82-7

Basic information

• Product Name: 2-(1-benzylpiperidin-4-ylidene)acetonitrile
• Synonyms: 2-(1-benzylpiperidin-4-ylidene)acetonitrile;2-(1-Benzyl-4-piperidylidene)acetonitrile;Acetonitrile, 2-[1-(phenylMethyl)-4-piperidinylidene]-;(1-Benzyl-4-piperidinylidene)acetonitrile
• CAS NO: 55022-82-7
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29024
• Mol File: 55022-82-7.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(1-benzylpiperidin-4-ylidene)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-benzylpiperidin-4-ylidene)acetonitrile(55022-82-7)
• EPA Substance Registry System: 2-(1-benzylpiperidin-4-ylidene)acetonitrile(55022-82-7)

Safety Data

• Hazardous Substances Data: 55022-82-7(Hazardous Substances Data)

Usage

General Description

2-(1-benzylpiperidin-4-ylidene)acetonitrile is a chemical compound that is a derivative of piperidine. It has the molecular formula C17H19N3 and a molar mass of 265.35 g/mol. 2-(1-benzylpiperidin-4-ylidene)acetonitrile is used in medicinal chemistry research as a potential drug candidate in the treatment of various neurological disorders and conditions. It may act as a central nervous system depressant and has the potential to interact with neurotransmitter receptors in the brain. The chemical structure of 2-(1-benzylpiperidin-4-ylidene)acetonitrile contains a piperidine ring, a benzyl group, and a nitrile functional group, which are important for its pharmacological activity.

Upstream product

• 41979-39-9 4-piperidone hydrochloride 
• 100-39-0 benzyl bromide 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

Downstream Products

• 1332498-42-6 2-(1-benzyl-piperidin-4-yl)-N-hydroxy-acetamidine 
• 1332498-43-7 N-[2-(1-benzyl-piperidin-4-yl)-1-hydroxyimino-ethyl]-3-(3,4-dimethoxy-phenyl)acrylamide 
• 1332498-44-8 1-benzyl-4-{5-[2-(3,4-dimethoxy-phenyl)-vinyl]-[1,2,4]oxadiazol-3-ylmethyl}piperidine 
• 1332498-45-9 4-{2-[3-(1-benzyl-piperidin-4-ylmethyl)-[1,2,4]oxadiazol-5-yl]-vinyl}-benzene-1,2-diol 
• 1609078-40-1 3-(1-benzylpiperidin-4-yl)-2-(((8-hydroxyquinolin-5-yl)methyl)(prop-2-ynyl)amino)propanenitrile 
• 1609078-46-7 3-(1-benzylpiperidin-4-yl)-2-(prop-2-yn-1-ylamino)propanenitrile 
• 120014-32-6 (1-benzylpiperidin-4-yl)acetaldehyde 
• 1609078-39-8 5-(((2-(1-benzylpiperidin-4-yl)ethyl)(prop-2-ynyl)amino)methyl)quinolin-8-ol 
• 1609078-45-6 N-[2-(1-benzylpiperidin-4-yl)ethyl]prop-2-yn-1-amine 
• 785783-14-4 [1-benzyl-4-(butylamino)piperidin-4-yl]acetonitrile 
• 78056-67-4 1-(phenylmethyl)-4-piperidineacetonitrile 

Relevant articles and documents

Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization

A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.

Multi-target-oriented protective agent neurocyte

PROBLEM TO BE SOLVED: To provide a promising multi target direction type pharmaceutical candidate molecule which is promising for treatments of Alzheimer-type dementia (AD), which is a molecule having good cell membrane permeability including blood brain barrier.SOLUTION: A compound designed by a conjunction method with which a benzylpiperidine part of an acetylcholine esterase (AChE) inhibitor, donepezil is connected through an oligomethylene linker and combined with a propargyl part having a monoamine oxidase(MAO) inhibition activity and 8-hydroxy-5-methylaminoquinoline functional group, i.e. a center nitrogen atom substituted by a pro-chelator motif of a biochemical metal, interacts with AChE and butyrylcholinesterase(BuChE), further MAOA and B.

Donepezil + propargylamine + 8-hydroxyquinoline hybrids as new multifunctional metal-chelators, ChE and MAO inhibitors for the potential treatment of Alzheimer's disease

The synthesis, biochemical evaluation, ADMET, toxicity and molecular modeling of novel multi-target-directed Donepezil + Propargylamine + 8-Hydroxyquinoline (DPH) hybrids 1-7 for the potential prevention and treatment of Alzheimer's disease is described. The most interesting derivative was racemic α-aminotrile4-(1-benzylpiperidin-4-yl)-2-(((8-hydroxyquinolin-5-yl) methyl)(prop-2-yn-1-yl)amino) butanenitrile (DPH6) [MAO A (IC50 = 6.2 ± 0.7 μM; MAO B (IC50 = 10.2 ± 0.9 μM); AChE (IC50 = 1.8 ± 0.1 μM); BuChE (IC50 = 1.6 ± 0.25 μM)], an irreversible MAO A/B inhibitor and mixed-type AChE inhibitor with metal-chelating properties. According to docking studies, both DPH6 enantiomers interact simultaneously with the catalytic and peripheral site of EeAChE through a linker of appropriate length, supporting the observed mixed-type AChE inhibition. Both enantiomers exhibited a relatively similar position of both hydroxyquinoline and benzyl moieties with the rest of the molecule easily accommodated in the relatively large cavity of MAO A. For MAO B, the quinoline system was hosted at the cavity entrance whereas for MAO A this system occupied the substrate cavity. In this disposition the quinoline moiety interacted directly with the FAD aromatic ring. Very similar binding affinity values were also observed for both enantiomers with ChE and MAO enzymes. DPH derivatives exhibited moderate to good ADMET properties and brain penetration capacity for CNS activity. DPH6 was less toxic than donepezil at high concentrations; while at low concentrations both displayed a similar cell viability profile. Finally, in a passive avoidance task, the antiamnesic effect of DPH6 was tested on mice with experimentally induced amnesia. DPH6 was capable to significantly decrease scopolamine-induced learning deficits in healthy adult mice.