145546-80-1

Basic information

• Product Name: 2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE
• Synonyms: Donepezil Related Compound A (25 mg) ((E)-2-[(1-benzylpiperidin-4-yl)methylene]-5,6-dimethoxyindan-1-one);Donepezil related coMpound A;(2E)-Dehydrodonepezil;Donepezil Related Compound A(USP);(2E)-Dehydrodonepezil\n\n(Donepezil Impurity)
• CAS NO: 145546-80-1
• Molecular Formula: C24H27 N O3
• Molecular Weight: 377.48
• Mol File: 145546-80-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 542.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.209±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.17±0.10(Predicted)
• CAS DataBase Reference: 2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE(145546-80-1)
• EPA Substance Registry System: 2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE(145546-80-1)

Safety Data

• Hazardous Substances Data: 145546-80-1(Hazardous Substances Data)

Usage

Description

2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE is a complex organic compound with a unique molecular structure. It is characterized by its indanone core, which is substituted with a 1-benzyl-4-piperidinyl group and a (E)-configuration of the double bond. The molecule also features two methoxy groups at the 5,6-positions, which may contribute to its potential applications.

Uses

Used in Pharmaceutical Industry:
2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE is used as a nootropic agent for enhancing cognitive function and memory. Its structure is derived from Donepezil, a known acetylcholinesterase inhibitor, which suggests that it may have similar mechanisms of action in improving cognitive performance.
Used in Research and Development:
In the field of medicinal chemistry, this compound serves as a valuable research tool for understanding the structure-activity relationships of nootropic agents and acetylcholinesterase inhibitors. It can be used to develop new drugs with improved efficacy and fewer side effects.
Used in Drug Synthesis:
As a derivative of Donepezil, 2-[(E)-(1-BENZYL-4-PIPERIDINYL)METHYLIDENE]-5,6-DIMETHOXY-1-INDANONE may be utilized in the synthesis of novel drugs with potential applications in the treatment of Alzheimer's disease and other cognitive disorders. Its unique structure could provide new insights into the design of more effective therapeutic agents.

Upstream product

• 2107-69-9 5,6-dimethoxy-1-indanone 
• 22065-85-6 N-benzyl-4-formylpiperidine 
• 1126-09-6 4-carbethoxypiperidine 
• 100-44-7 benzyl chloride 
• 24228-40-8 N-benzyl isonipecotic acid ethyl ester 
• 67686-01-5 1-benzyl-4-piperidinemethanol 
• 4693-38-3 3-chloro-1-(3,4-dimethoxyphenyl)propan-1-one 
• 1025909-53-8 (1-benzylpiperidin-2-yl)acetaldehyde 
• 77034-34-5 ethyl N-benzylpipecolinate 
• 134256-32-9 N-benzyl-2-(2-hydroxyethyl)piperidine 
• 100-52-7 benzaldehyde 
• 2107-70-2 3,4-methoxycinnamic acid 
• 197010-20-1 2-((1-benzyl-piperidin-4-yl)-hydroxymethyl)-5,6-dimethoxyindan-1-one 
• 2747-08-2 2-bromo-5,6-dimethoxy-1-indanone 

Relevant articles and documents

Synthetic method of donepezil hydrochloride

The invention belongs to the technical field of medicines, and discloses a synthetic method of donepezil hydrochloride. The method comprises the following steps: taking 5, 6-dimethoxy-1-indanone and 4-pyridylaldehyde as initial raw materials, generating a

Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow

A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.