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  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls

Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (CAS No. 130753-13-8): A Comprehensive Overview

Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (CAS No. 130753-13-8) is a complex organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique bicyclic structure and the presence of a benzyl ester group, exhibits a range of biological activities that make it a valuable candidate for various therapeutic applications.

The chemical structure of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate is composed of an 8-azabicyclo[3.2.1]octane core, which is a nitrogen-containing bicyclic system, and a benzyl ester moiety attached to the carboxylic acid group at the 8-position. The presence of the oxo group at the 3-position adds to the compound's structural complexity and contributes to its unique pharmacological properties.

Recent studies have highlighted the potential of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate in various therapeutic areas, including neurodegenerative diseases, cancer, and inflammatory disorders. One notable area of research is its role as a modulator of G protein-coupled receptors (GPCRs), which are key targets in drug discovery and development.

In a study published in the Journal of Medicinal Chemistry, researchers investigated the binding affinity and selectivity of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate for several GPCRs, including serotonin receptors (5-HT_2A and 5-HT_2C) and dopamine receptors (D₂). The results showed that this compound exhibited high affinity and selectivity for these receptors, suggesting its potential as a lead compound for the development of novel drugs targeting these pathways.

Furthermore, Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate has been studied for its anti-inflammatory properties. In vitro experiments using human peripheral blood mononuclear cells (PBMCs) demonstrated that this compound effectively inhibited the production of pro-inflammatory cytokines such as TNF-alpha and IL-6, indicating its potential use in treating inflammatory conditions like rheumatoid arthritis and multiple sclerosis.

The pharmacokinetic properties of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate have also been evaluated in preclinical studies. These studies revealed that the compound exhibits favorable oral bioavailability and a reasonable half-life, making it suitable for further development as an oral therapeutic agent.

In addition to its therapeutic potential, Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate has been explored for its use as a synthetic intermediate in the preparation of other bioactive compounds. Its versatile chemical structure allows for easy functionalization, making it a valuable building block in organic synthesis.

The synthesis of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate has been optimized through various synthetic routes, with recent advancements focusing on improving yield and reducing environmental impact. One such method involves the use of transition-metal-catalyzed reactions to construct the bicyclic core efficiently.

The safety profile of Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate has been extensively evaluated in preclinical toxicology studies. These studies have shown that the compound is well-tolerated at therapeutic doses, with no significant adverse effects observed in animal models.

In conclusion, Benzyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (CAS No. 130753-13-8) is a promising compound with a wide range of potential applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure, combined with its favorable pharmacological properties, makes it an attractive candidate for further development as a therapeutic agent or synthetic intermediate.

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