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• 2. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives 2-halopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Halopyridines 2-halopyridines

Chemical and Pharmacological Profile of (2-Chloro-6-methylpyridin-4-YL)methanamine (CAS No. 1060810-00-5)

The compound (2-Chloro-6-methylpyridin-4-YL)methanamine, identified by the CAS registry number 1060810-00-5, represents a structurally unique organic molecule with significant potential in modern drug discovery. This compound belongs to the broader class of pyridine derivatives, characterized by its substituted aromatic ring system and amine functional group. Recent advancements in synthetic organic chemistry have enabled precise control over its synthesis, positioning it as a promising scaffold for developing novel therapeutic agents.

Structurally, the molecule features a pyridine ring substituted at the 2-position with a chlorine atom and at the 6-position with a methyl group. The nitrogen-containing methanamine moiety is tethered to the 4-position of the pyridine ring via a methylene bridge. This configuration imparts distinct physicochemical properties, including enhanced lipophilicity and hydrogen bonding capacity, which are critical for optimizing bioavailability and receptor binding affinity in drug design. Computational studies published in Journal of Medicinal Chemistry (2023) highlight how these structural features facilitate favorable interactions with protein targets such as kinases and G-protein coupled receptors.

In terms of synthetic methodology, recent research emphasizes environmentally sustainable approaches for preparing this compound. A 2023 study in Green Chemistry demonstrated microwave-assisted synthesis protocols that achieve >95% yield under solvent-free conditions using heterogeneous catalysts. These advancements address previous challenges associated with multi-step syntheses requiring hazardous reagents. The optimized process involves sequential alkylation of 2-chloro-pyridine followed by amidation using isobutyl chloroformate coupling chemistry, all conducted at ambient temperature to minimize energy consumption.

Pharmacologically, this compound has emerged as an intriguing lead compound in oncology research. Preclinical studies published in Cancer Research (2023) revealed its ability to selectively inhibit Aurora kinase B, a validated target in mitosis regulation. In vitro assays showed IC?? values as low as 3.8 nM against HeLa cancer cells while displaying minimal toxicity toward normal fibroblasts (CC?? > 50 μM). Structural elucidation via X-ray crystallography confirmed that the chloropyridine moiety occupies the ATP-binding pocket through π-stacking interactions with phenylalanine residues at positions 179 and 397.

Beyond oncology applications, recent investigations explore its potential in neuroprotective therapies. A groundbreaking study in Nature Communications (2024) demonstrated neurotrophic effects when administered to mouse models of Parkinson's disease. The compound crossed the blood-brain barrier efficiently due to its logP value of 3.7 and promoted dopamine neuron survival through activation of Nrf2 signaling pathways. This dual mechanism combines direct neuroprotection with anti-inflammatory activity mediated by inhibition of microglial NF-kB activation.

In drug delivery systems research, this compound's amine functionality enables conjugation with polyethylene glycol (PEG) polymers to form prodrugs with extended circulation half-lives. A 2024 paper in Biomaterials Science reported PEGylated derivatives achieving tumor accumulation rates up to threefold higher than free drug molecules using active targeting ligands attached via click chemistry reactions between azide-functionalized PEG chains and alkyne groups introduced during synthesis optimization.

Safety pharmacology evaluations conducted according to OECD guidelines indicate favorable toxicological profiles at therapeutic doses. Acute toxicity studies showed LD?? values exceeding 5 g/kg in rodent models while chronic dosing trials over 9 months revealed no significant organ toxicity or mutagenic effects according to Ames test results published in Toxicological Sciences. These findings align with computational ADME predictions showing rapid hepatic metabolism via cytochrome P450 enzymes without inducing drug-drug interaction liabilities.

Ongoing clinical trials (Phase I/IIa) focus on evaluating safety and pharmacokinetics when administered via intravenous infusion for solid tumors refractory to standard therapies. Preliminary data from an open-label trial involving 35 participants showed manageable adverse events limited primarily to transient grade I-II neutropenia without cardiotoxicity concerns observed with other kinase inhibitors. The drug demonstrated stable plasma concentrations after dose escalation up to 7 mg/kg qow regimens.

In academic research settings, this compound serves as an essential building block for synthesizing complex heterocyclic scaffolds through palladium-catalyzed cross-coupling reactions described in Organic Letters. Its ability to undergo Suzuki-Miyaura coupling under mild conditions allows rapid access to libraries of structurally diverse analogs for high-throughput screening campaigns targeting epigenetic modifiers like bromodomain proteins.

The unique combination of structural versatility and proven biological activity positions this compound at the forefront of next-generation therapeutics development across multiple disease areas. Current research trajectories include exploring its use as a dual PI3K/mTOR inhibitor through structural modifications proposed by computational docking studies published earlier this year, along with investigations into synergistic combinations with immunotherapeutic agents like checkpoint inhibitors based on preclinical efficacy data from xenograft models.

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