• 1. Fast synthesis of red Li3BaSrLn3(WO4)8:Eu3+ phosphors for white LEDs under near-UV excitation by a microwave-assisted solid state reaction method and photoluminescence studies
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• 2. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
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• 3. Fe3O4/Au/Fe3O4 nanoflowers exhibiting tunable saturation magnetization and enhanced bioconjugation
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• 4. Dissolution of cork biopolymers in biocompatible ionic liquids
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• 5. Emerging 2D hybrid nanomaterials: towards enhanced sensitive and selective conductometric gas sensors at room temperature
  Hanie Hashtroudi,Ian D. R. Mackinnon J. Mater. Chem. C, 2020,8, 13108-13126

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

(3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine (CAS No. 872492-59-6: A Versatile Scaffold in Modern Medicinal Chemistry

(3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine (CAS No. 872492-59-6) is a structurally diverse heterocyclic compound that has garnered significant attention in the field of medicinal chemistry due to its unique pyridine ring framework and the presence of a 3-bromo-5-methyl substitution pattern. This compound, which contains a pyridin-2-yl group attached to a methylamine moiety, serves as a valuable building block in the synthesis of bioactive molecules. Its pyridine ring, a six-membered aromatic heterocycle with one nitrogen atom, is a common structural motif in many pharmaceutical agents, including antineoplastic drugs, antiviral agents, and neuroprotective compounds. The 3-bromo and 5-methyl substituents on the pyridine ring introduce steric and electronic effects that can be strategically exploited to modulate the reactivity and biological activity of derivatives synthesized from this compound.

The pyridine ring in (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is a key pharmacophore that exhibits strong hydrogen-bonding capabilities and favorable electronic properties, making it an attractive target for functionalization. The 3-bromo substituent, in particular, offers a versatile handle for regioselective substitution reactions, enabling the introduction of a wide range of functional groups. This feature is especially relevant in drug discovery campaigns where the optimization of ligand efficiency and selectivity profiles is critical. Recent studies have demonstrated that pyridine-based compounds can act as modulators of protein-protein interactions, inhibitors of kinases, and ligands for G-protein coupled receptors (GPCRs), highlighting their broad therapeutic potential.

One of the most notable applications of (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine lies in its role as a precursor in the synthesis of small-molecule inhibitors targeting tyrosine kinase receptors, which are implicated in various oncogenic pathways. The 3-bromo group can be readily converted into amine, hydroxyl, or carboxylic acid functionalities through transition-metal-catalyzed cross-coupling reactions, such as Suzuki-Miyaura or Stille couplings. These transformations are pivotal in the development of targeted therapies for solid tumors and hematologic malignancies. For instance, a 2023 study published in JACS reported the use of pyridine-based scaffolds in the design of ATP-competitive inhibitors for EGFR (epidermal growth factor receptor) mutants, which are resistant to first-generation tyrosine kinase inhibitors.

The 5-methyl substitution on the pyridine ring of (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine also contributes to its chemical stability and solubility profiles, which are essential considerations in drug formulation and in vivo pharmacokinetics. This substitution pattern has been shown to enhance the lipophilicity of derivatives, facilitating their cell membrane penetration and target engagement. Moreover, the methylamine group attached to the pyridine ring provides a flexible linkage that can be tailored to improve binding affinity to enzyme active sites or receptor binding pockets. This adaptability has made (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine a popular choice in hit-to-lead campaigns for central nervous system (CNS) disorders, where blood-brain barrier permeability is a critical parameter.

In the context of neurodegenerative diseases, such as Alzheimer's disease and Parkinson's disease, pyridine-based compounds have been explored as acetylcholinesterase inhibitors and mitochondrial modulators. A 2024 review in ACS Chemical Neuroscience highlighted the potential of pyridine derivatives to regulate oxidative stress and mitochondrial dysfunction, which are central to the pathogenesis of these conditions. The 3-bromo and 5-methyl substituents in (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine may further enhance these properties by modulating redox homeostasis and apoptotic signaling pathways. These findings underscore the importance of structure-activity relationship (SAR) studies in optimizing lead compounds derived from this scaffold.

Another emerging area of research involving (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is its application in antimicrobial drug development, particularly against multidrug-resistant pathogens. The pyridine ring has been shown to exhibit intrinsic antimicrobial activity through disruption of bacterial cell membranes and inhibition of essential enzymes. In a 2023 study published in Antimicrobial Agents and Chemotherapy, a series of pyridine-based compounds were found to effectively inhibit Mycobacterium tuberculosis by targeting the mycolic acid biosynthesis pathway, a key virulence factor in the bacterium. The 3-bromo and 5-methyl substituents in (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine may enhance these effects by increasing membrane permeability or enzyme inhibition potency.

From a synthetic chemistry perspective, (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is a versatile building block that can be functionalized via a variety of reaction conditions. The 3-bromo group is compatible with nucleophilic substitution, electrophilic aromatic substitution, and metal-catalyzed coupling reactions, providing access to a diverse array of heterocyclic systems and conjugated π-systems. These transformations are particularly valuable in the construction of complex molecules for biological screening and target validation. For example, the methylamine group can be converted into carboxylic acids, esters, or amides through oxidative cleavage or selective functionalization, enabling the synthesis of peptidomimetics and prodrug precursors.

Looking ahead, the continued exploration of (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine and its derivatives is expected to yield novel therapeutics across multiple therapeutic areas. Advances in computational modeling and machine learning are likely to accelerate the optimization of substituent patterns and predictive design of bioactive molecules. Furthermore, green chemistry approaches, such as solvent-free reactions and biocatalytic methods, may be employed to improve the sustainability and scalability of syntheses involving this compound. As the field of drug discovery continues to evolve, (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is poised to remain a cornerstone in the development of next-generation medicines that address unmet clinical needs.

The compound (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is a versatile and chemically rich scaffold with significant potential in medicinal chemistry and drug discovery. Its unique structural features—namely, the 3-bromo and 5-methyl substituents on the pyridine ring, as well as the methylamine group—contribute to its adaptability in various synthetic transformations and biological applications. Below is a structured summary of its key attributes, applications, and future directions: --- ### 1. Structural Features and Synthetic Versatility - Pyridine Ring: The core aromatic system provides stability and electron-deficient characteristics, facilitating electrophilic and nucleophilic reactions. - 3-Bromo Substituent: A highly reactive electrophilic site, enabling nucleophilic substitution (e.g., with amines, alcohols), electrophilic aromatic substitution, and transition-metal-catalyzed coupling reactions (e.g., Buchwald–Hartwig amination, Suzuki coupling). - 5-Methyl Substituent: Introduces steric and electronic effects, potentially modulating reactivity and biological activity. - Methylamine Group: Offers flexibility for oxidative cleavage (to carboxylic acids, esters, or amides), alkylation, or peptidomimetic construction. --- ### 2. Biological Applications and Therapeutic Potential #### a) Anticancer Agents - Mechanism: The pyridine ring and bromo/methyl substituents may interact with DNA, enzymes (e.g., kinases), or cell signaling pathways. - Examples: Derivatives have been explored as DNA intercalators, topoisomerase inhibitors, and apoptosis inducers. #### b) Neurodegenerative Diseases - Mechanism: Modulation of redox homeostasis, mitochondrial function, and neuroinflammation. - Examples: Potential applications in Alzheimer’s, Parkinson’s, and multiple sclerosis. #### c) Antimicrobial Agents - Mechanism: Disruption of bacterial cell membranes and inhibition of essential enzymes (e.g., mycolic acid biosynthesis in *M. tuberculosis*). - Examples: Effective against multidrug-resistant pathogens. #### d) Peptidomimetics and Prodrugs - Mechanism: The methylamine group can be converted into carboxylic acids, esters, or amides, enabling the synthesis of peptidomimetics and prodrug precursors. --- ### 3. Synthetic Chemistry and Reaction Pathways - Nucleophilic Substitution: Bromo group can be replaced with amines, alcohols, or thiols. - Electrophilic Aromatic Substitution: Introduce nitro, sulfonyl, or halogen groups. - Coupling Reactions: - Buchwald–Hartwig amination: Form C–N bonds. - Suzuki–Miyaura coupling: Introduce aryl or vinyl groups. - Sonogashira coupling: Add alkynyl groups. - Oxidative Cleavage: Convert methylamine to carboxylic acids (e.g., via Swern oxidation or Dess–Martynoff oxidation). --- ### 4. Future Directions and Innovations - Computational Modeling: Use of AI and machine learning to predict optimal substituent patterns and drug-target interactions. - Green Chemistry: Adoption of solvent-free reactions, biocatalytic methods, and catalyst recycling to improve sustainability. - Multifunctional Molecules: Design of hybrid therapeutics that combine antimicrobial, anticancer, and anti-inflammatory activities. - Prodrug Strategies: Development of prodrugs with enhanced bioavailability and tissue specificity. --- ### 5. Conclusion (3-Bromo-5-methyl-pyridin-2-yl)-methyl-amine is a highly versatile scaffold with broad synthetic and biological potential. Its adaptability in chemical transformations, coupled with its promising therapeutic applications, positions it as a cornerstone in the development of next-generation medicines. Continued research in structure-activity relationships (SAR), computational drug design, and sustainable synthetic methods will further unlock its full potential in addressing unmet clinical needs across diverse therapeutic areas.

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