146274-40-0

Usage

Uses

Used in Pharmaceutical Industry:
(3α)-3-Deoxy-3-chlorogalanthaMine is used as a pharmaceutical agent for its AChE inhibitory properties. It serves as a crucial component in the development of drugs targeting cognitive disorders and neurodegenerative diseases, such as Alzheimer's disease, where the inhibition of AChE is essential for enhancing cognitive function and memory.
Used in Research and Development:
In the field of scientific research, (3α)-3-Deoxy-3-chlorogalanthaMine is utilized as a key compound for studying the mechanisms of AChE inhibition and its potential applications in the treatment of various cognitive impairments. Its chemical properties and structure make it an ideal candidate for further investigation and development of novel therapeutic strategies.
Used in Drug Design and Synthesis:
(3α)-3-Deoxy-3-chlorogalanthaMine is employed as a starting material or a structural template in the design and synthesis of new AChE inhibitors and other related compounds. Its unique chemical properties allow researchers to explore its potential in creating more effective and targeted drugs for the treatment of cognitive disorders.

Upstream product

• 357-70-0 Galantamine 
• 1953-04-4 Galantamine hydrobromide 

Downstream Products

• 312920-69-7 (-)-3-deoxygalanthamine 
• 357-70-0 Galantamine 
• 312920-77-7 1-hydroxy-2-phenylseleno-3-deoxylycoramine 

Relevant academic research and scientific papers

Synthesis of 6β-D-glucosyl and 6-nitroxy (-)-galanthamine derivatives as acetylcholinesterase inhibitors

Galanthamine is an alkaloid approved for the treatment of Alzheimer's disease. In this paper the syntheses and the anticholinesterase activities of new glucosyl and nitroxy derivatives substituted on position 6 are reported. Compounds 2, 3 and 5 presented a percentage of inhibition of 35.22%, 47.48% and 67.89 % respectively.

Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine

An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.

Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease ?

We conducted structural and pharmacological studies of galanthamine, a cortical acetylcholinesterase (AChE) inhibitor, and 19 structural analogs.Systematic derivatization of galanthamine at the cyclohexene ring, tertialy amino, hydroxyl, methoxyl functions indicated that these structural features are essential for biological activity.Molecular modeling studies suggested that the low energy conformations of the analogs are similar to that of the parent.One derivative, galanthamine n-butyl carbamate, had an LD50 of over 100 mg/kg (ip) in mice.In a passive avoidanceparadigm, this analog improved performance in a dose-dependant fashion with a peak effect at 0.1 mg/kg in control and 0.5 mg/kg in basal forebrain lesioned mice.In the same paradigm, the peak effect of the parent compound is a 6-fold higher dose.With this surprisingly high therapeutic ratio, this compound may be of interest in treating cholinergic deficits of the central nervous system such as Alzheimer's desease. galanthamine derivatives / molecular modeling / avetylcholinesterase inhibitor / Alzheimer's desease / passive avoidance / basal forebrain lesion