142852-50-4

Usage

Uses

Used in Pharmaceutical Industry:
ZANAPEZIL is used as a therapeutic agent for the treatment of Alzheimer's disease. It is particularly effective in managing the cognitive decline and memory impairment associated with the condition by increasing the levels of acetylcholine in the brain, thus potentially improving cognitive function and memory.

InChI:InChI=1/C25H32N2O/c28-25(23-11-10-22-8-4-5-15-26-24(22)18-23)12-9-20-13-16-27(17-14-20)19-21-6-2-1-3-7-21/h1-3,6-7,10-11,18,20,26H,4-5,8-9,12-17,19H2

Upstream product

• 32281-97-3 7-bromo-3,4-dihydro-2H-naphthalen-1-one 
• 54288-70-9 4-bromopiperidine hydrobromide 
• 885953-12-8 8-bromo-1,3,4,5-tetrahydro-2H-benzo[b]azepin-2-one 
• 142853-11-0 3-(1-acetyl-4-piperidinyl)-1-(1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone 
• 142853-09-6 3-(1-acetyl-4-piperidinyl)propionyl chloride 
• 19886-89-6 1-Acetyl-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 100-39-0 benzyl bromide 
• 142852-16-2 3-(piperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-benzo[b]azepin-8-yl)propan-1-one 

Downstream Products

• 142852-98-0 1-Acetyl-8-[1-oxo-3-[1-(phenylmethyl)piperidin-4-yl]propyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 

Relevant academic research and scientific papers

Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade

We report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl bromides. Concise formal synthesis of Zanapezil is achieved using this β-alkylation method.

Central Cholinergic Agents. 6. Synthesis and Evaluation of 3--1-(2,3,4,5-tetrahydro-1H-benzazepin-8-yl)-1-propanones and Their Analogs as Central Selective Acetylcholinesterase Inhibitors

In an attempt to find central selective acetylcholinesterase (AChE) inhibitors, 3--1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanones 9 and their analogs were designed on the basis of our working hypothesis of the enzyme's active site.These compounds were prepared by regioselective Fridel-Crafts acylation of 2,3,4,5-tetrahydro-1H-1-benzazepines and related nitrogen heterocycles as a key step.Most compounds showed potent inhibitory activities with IC50s in the 10-300 nM range.In order to estimate their central selectivities, we examined their effects on the apomorphine-induced circling behavior in rats with unilateral striatal lesions.Among compounds with potent AChE inhibition, 3--1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone fumarate (9a, TAK-147) (IC50 of AChE inhibition = 97.7 nM) inhibited the circling behavior at 3 mg/kg po, in which it had no significant effect on peripheral cholinergic effects.This demonstrates that 9a has favorable central selectivity.Furthermore, 9a significantly ameliorated diazepam-induced passive avoidance deficit at 1 mg/kg po.The benzazepine derivative 9a was selected as a candidate for clinical evaluation.