231283-82-2

Basic information

• Product Name: 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-yl)methylpyridinium Bromide
• Synonyms: 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-yl)methylpyridinium Bromide
• CAS NO: 231283-82-2
• Molecular Formula: C24H24BrNO3
• Molecular Weight: 454.35626
• Product Categories: Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 231283-82-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-yl)methylpyridinium Bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-yl)methylpyridinium Bromide(231283-82-2)
• EPA Substance Registry System: 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-yl)methylpyridinium Bromide(231283-82-2)

Safety Data

• Hazardous Substances Data: 231283-82-2(Hazardous Substances Data)

Upstream product

• 2107-69-9 5,6-dimethoxy-1-indanone 
• 877606-65-0 (E)-5, 6-dimethoxy-2-(pyridin-4-ylmethylene)-2, 3-dihydro-1H-inden-1-one 
• 872-85-5 pyridine-4-carbaldehyde 
• 4803-57-0 2-(pyridin-4-yl)methyl-5,6-dimethoxy-1-indanone 
• 100-39-0 benzyl bromide 

Relevant articles and documents

Donepezil-Based Central Acetylcholinesterase Inhibitors by Means of a "bio-Oxidizable" Prodrug Strategy: Design, Synthesis, and in Vitro Biological Evaluation

With the aim of reducing side effects of acetylcholinesterase inhibitors (AChEIs) during symptomatic treatment of Alzheimer's disease, we report herein a new class of donepezil-based "bio-oxidizable" prodrugs 1 designed to be converted into dual binding site AChEIs 2. While most of indanone-derived N-benzylpyridinium salts 2 revealed to be highly potent dual binding site hAChEIs (IC50 up to 3 nM), outperforming the standard drug donepezil (IC50 = 11 nM), most of the corresponding 1,4-dihydropyridines 1 were found to be inactive. Promisingly, whereas the selected prodrug 1r showed good permeability in the PAMPA-BBB model and high in vitro antioxidant activity, its conversion to AChEI 2r could be easily achieved under mild conditions when incubated in various oxidizing media. Lastly, both compounds 1r and 2r did not show genotoxicity in vitro and displayed high LD50 values in mice, making this prodrug 1r/drug 2r couple a good candidate for further in vivo biological experiments.

Acetylcholinesterase inhibitors containing 1-benzyl-pyridinium salts

The present invention provides an excellent acetylcholinesterase inhibitor. That is, it provides an acetylcholinesterase inhibitor comprising a 1-benzylpyridinium salt represented by the following formula: wherein R1, R2, R3 and R4 are the same as or different from each other and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitrile group, a C1-6 alkyl group, a C1-6 alkoxy group etc.; R5 represents a hydrogen atom, a halogen atom etc.; the partial structure: is a group represented by the formula >C(R6)—CH2— (wherein R6 is a hydrogen atom or a halogen atom) or >C═CH—; X?represents a halide ion or organic sulfonic acid ion; and m is 0 or an integer from 1 to 5.

Process for production of donepezil derivative

The present invention provides a novel industrially or economically preferable process for production of a hydrogen halogenide salt of a Donepezil derivative having an excellent pharmacological action as medicament, namely, reaction of 1-indanone derivative with carbonate ester to obtain 2-alkoxycarbonyl-1-indanone derivative, followed by reaction with halogenated (4-pyridyl)methyl or a salt thereof and decarboxylation successively to obtain 2-(4-pyridyl)methyl-1-indanone derivative, then reaction with halogenated benzyl to obtain quaternary ammonium salt, then reduction, and synthetic intermediates thereof. (Wherein R1represents a hydrogen atom or lower alkoxy; n represents an integer of 1 to 4; R2represents lower alkyl group; and X represents a halogen atom.)