5176-21-6

Usage

Uses

Used in Pharmaceutical Industry:
1-Azabicyclo[2.2.2]octane-3-carboxaldehyde is used as a precursor in the synthesis of various pharmaceuticals due to its unique bicyclic structure and aldehyde functionality, which can be further modified to create a wide range of bioactive compounds.
Used in Agrochemical Industry:
1-Azabicyclo[2.2.2]octane-3-carboxaldehyde is used as a starting material for the production of agrochemicals, such as pesticides and herbicides, leveraging its reactivity and structural features to develop new and effective compounds for agricultural applications.
Used in Heterocyclic Compound Synthesis:
1-Azabicyclo[2.2.2]octane-3-carboxaldehyde is used as a building block for the synthesis of heterocyclic compounds, which are important in various fields, including medicinal chemistry, materials science, and pharmaceuticals, due to their diverse chemical properties and potential applications.
Used in Medicinal Chemistry Research:
1-Azabicyclo[2.2.2]octane-3-carboxaldehyde is being studied for its potential biological activity and applications in the field of medicinal chemistry, as its unique structure and functional groups may contribute to the development of new therapeutic agents and drug candidates.

Upstream product

• 105284-91-1 3-[1-Methoxy-meth-(Z)-ylidene]-1-aza-bicyclo[2.2.2]octane 
• 51627-76-0 3-Cyano-1-azabicyclo[2.2.2]octane 
• 3731-38-2 3-Quinuclidinone 
• 242810-00-0 3-Methoxymethylquinuclidine-3-ol 

Downstream Products

• 2643-30-3 3-Vinylquinuclidine 
• 5176-22-7 3-hydroxymethyl-1-azabicyclo[2.2.2]octane 
• 160126-78-3 Z-3-[2-(4-butoxyphenyl)vinyl]-quinuclidine 

Relevant academic research and scientific papers

Design of [R-(Z)]-(+)-α-(methoxyimino)-1-azabicyclo[2.2.2]octane-3- acetonitrile (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester bioisostere

Loss of cholinergic function is believed to be implicated in the cognitive decline associated with senile dementia of the Alzheimer type (SDAT). The disease is characterized by progressive loss of muscarinic receptors located on nerve terminals while postsynaptic muscarinic M1 receptors appear to remain largely intact. Muscarinic agonists acting directly on postsynaptic receptors offer the prospect of countering the cholinergic deficit in SDAT. This study describes a novel series of azabicyclic muscarinic agonists, which incorporate an oxime ether or modified oxime ether group as an ester bioisotere. Modification of the oxime ether function by the introduction of electron withdrawing groups led to the finding that the (Z)-N-methoxy imidoyl nitrile group serves as a stable methyl ester bioisostere. This culminated in the discovery of the quinuclidinyl N-methoxy imidoyl nitrile (R)-(+)-(Z)-5g which is a functionally selective muscarinic M1 partial agonist currently in phase III clinical trials for the treatment of SDAT. The selective profile of R-(+)- (Z)-5g can be rationalized in terms of the relative affinity of the compound at muscarinic receptor subtypes, the degree of agonist efficacy, and brain penetrancy.

FACILE SYNTHESIS OF STYRYLQUINUCLIDINES

3- and 2-Quinuclidinecarboxaldehydes, 3 and 12, were prepared by Wittig reaction and DIBAH reduction respectively.These aldehydes were used to prepare the corresponding 3- and 2-styrylquinuclidines, 4-7 and 13-16, via Wittig reactions.