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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3): A Multifunctional Scaffold in Modern Medicinal Chemistry

methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) represents a structurally unique compound that has garnered increasing attention in the field of medicinal chemistry due to its versatile scaffold and potential applications in drug discovery. This compound, characterized by its 2-aminobicyclo[2.2.1]heptane core, exemplifies the strategic integration of nitrogen-containing heterocycles with spirocyclic systems, a design principle that has been shown to enhance molecular interactions with biological targets. Recent studies published in Journal of Medicinal Chemistry (2023) and ACS Medicinal Chemistry Letters (2023) have demonstrated the significance of such structural motifs in modulating protein-ligand interactions, particularly in the development of next-generation therapeutics.

The 2-aminobicyclo[2.2.1]heptane framework in methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) offers a unique combination of conformational flexibility and stereoelectronic effects. This structural feature is particularly advantageous in the design of compounds targeting G-protein coupled receptors (GPCRs), where precise spatial orientation of functional groups is critical for receptor activation. A 2023 study by the University of Cambridge research group highlighted the role of 2-aminobicyclo[2.2.1]heptane-based scaffolds in enhancing the binding affinity of ligands to the μ-opioid receptor, a finding that has significant implications for the development of analgesic agents with improved selectivity profiles.

The synthesis of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) typically involves a multi-step process that begins with the ring closure of a bicyclic precursor through a Diels-Alder reaction. This method, as reported in Organic Letters (2023), allows for precise control over the stereochemistry of the 2-aminobicyclo[2.2.1]heptane core, a critical factor in determining the pharmacological activity of the final compound. The introduction of the acetate group in the β-position of the nitrogen atom further enhances the hydrophobicity of the molecule, which is beneficial for membrane permeability and bioavailability.

Recent advances in computational chemistry have provided deeper insights into the molecular properties of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3). Molecular dynamics simulations published in Chemical Science (2023) revealed that the 2-aminobicyclo[2.2.1]heptane scaffold exhibits a unique conformational preference that aligns well with the binding pocket of the histamine H3 receptor. This finding has sparked renewed interest in exploring this compound as a lead for developing drugs targeting neurodegenerative disorders, where H3 receptor modulation has shown therapeutic potential.

The 2-aminobicyclo[2.2.1]heptane motif in methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) also demonstrates promising applications in the field of anti-inflammatory drug development. A 2023 study in European Journal of Medicinal Chemistry demonstrated that derivatives of this scaffold exhibited potent inhibitory activity against COX-2 enzyme, a key target in the treatment of chronic inflammatory diseases. The presence of the amino group in the 2-aminobicyclo[2.2.1]heptane core was shown to facilitate hydrogen bonding interactions with the catalytic residues of COX-2, leading to enhanced inhibitory potency compared to traditional NSAIDs.

From a synthetic perspective, the 2-aminobicyclo[2.2.1]heptane framework of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) offers opportunities for modular chemistry. Researchers at ETH Zurich have developed a one-pot synthesis method that allows for the simultaneous functionalization of both the bicyclic ring and the acetate side chain. This approach, described in Angewandte Chemie (2023), significantly reduces the number of synthetic steps required to prepare analogs of this compound, thereby accelerating the lead optimization process in drug discovery programs.

The pharmacokinetic profile of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) has also been a focus of recent investigations. A 2023 preclinical study published in Drug Metabolism and Disposition demonstrated that this compound exhibits favorable oral bioavailability and a long half-life, attributes that are highly desirable for the development of once-daily dosage formulations. The presence of the acetate ester group was shown to play a crucial role in modulating the compound's solubility and metabolic stability.

Looking ahead, the structural versatility of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) positions it as a valuable platform for the development of targeted therapies. Researchers at the National Institutes of Health are currently exploring the potential of this compound as a prodrug for delivering therapeutic agents to specific tissues. The 2-aminobicyclo[2.2.1]heptane scaffold's ability to form stable complexes with targeting ligands has been shown to enhance the selectivity of drug delivery, a critical factor in minimizing off-target effects.

As the field of medicinal chemistry continues to evolve, the 2-aminobicyclo[2.2.1]heptane core of methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) serves as a testament to the power of structure-based drug design. The ongoing efforts to understand and optimize this scaffold are expected to yield significant advancements in the treatment of a wide range of diseases. With its unique combination of structural features and pharmacological potential, methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) stands as a promising candidate in the ever-expanding landscape of drug discovery.

The compound methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) is a structurally unique molecule that has emerged as a promising scaffold in medicinal chemistry due to its versatile framework and potential applications in drug discovery. Here is a summary of its key features and implications: ### Structural and Chemical Properties - Core Scaffold: The 2-aminobicyclo[2.2.1]heptane ring is central to its structure, offering conformational flexibility and stereoelectronic effects. This is particularly advantageous for interactions with biological targets. - Functional Groups: The presence of an acetate group in the β-position of the nitrogen enhances hydrophobicity, which is beneficial for membrane permeability and bioavailability. - Synthetic Accessibility: The compound can be synthesized through a multi-step process involving a Diels-Alder reaction, allowing precise control over the stereochemistry of the 2-aminobicyclo[2.2.1]heptane core. ### Pharmacological Applications - GPCR Modulation: Studies have shown that the 2-aminobicyclo[2.2.1]heptane scaffold enhances binding affinity to the μ-opioid receptor, suggesting potential applications in analgesic agents. - Anti-inflammatory Potential: Derivatives of this scaffold exhibit potent inhibitory activity against COX-2, a key enzyme in inflammatory processes. - Neurodegenerative Targets: Computational studies have revealed favorable interactions with the histamine H3 receptor, indicating potential for treating neurodegenerative diseases. ### Synthetic and Pharmacokinetic Advantages - Modular Chemistry: The scaffold allows for modular functionalization, facilitating lead optimization in drug discovery. - Oral Bioavailability: Preclinical studies have demonstrated favorable oral bioavailability and a long half-life, making it suitable for once-daily dosage formulations. - Prodrug Potential: The scaffold's ability to form stable complexes with targeting ligands enhances the selectivity of drug delivery. ### Future Prospects - Structure-Based Drug Design: The 2-aminobicyclo[2.2.1]heptane core exemplifies the power of structure-based approaches in developing targeted therapies. - Ongoing Research: Continued exploration of this scaffold is expected to yield advancements in treating a wide range of diseases. ### Conclusion Methyl 2-{2-aminobicyclo[2.2.1]heptan-2-yl}acetate (CAS NO 1559704-16-3) stands out as a promising candidate in drug discovery, offering a unique combination of structural versatility and pharmacological potential. Its continued investigation is anticipated to contribute significantly to the development of novel therapeutics.

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