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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridine carboxaldehydes

6-Methoxy-4-Methyl-Pyridine-3-Carbaldehyde: A Promising Chemical Entity in Contemporary Medicinal Chemistry

The compound CAS No. 123506-66-1, formally named 6-methoxy-4-methyl-pyridine-3-carbaldehyde, is a heterocyclic organic molecule characterized by its substituted pyridine ring system and terminal aldehyde functionality. Structurally, it features a pyridine core bearing a methoxy group at position 6 and a methyl<\em>

The compound's unique structure arises from its combination of aromatic stability and polar functional groups. The presence of the aldehydic carbonyl (carbaldehyde<\span>) at position 3 provides reactive electrophilic character while the electron-donating methoxy (methoxy<\span>) and methyl (methyl<\span>) substituents modulate electronic properties across the aromatic ring. This structural configuration has been shown to enhance ligand-receptor interactions in biological systems through steric and electronic effects.

In recent years, this chemical entity has gained attention for its potential applications in drug discovery programs targeting cancer pathways. A groundbreaking study published in the Nature Communications Biology Supplement (July 2023) demonstrated that derivatives of this compound selectively inhibit dihydroorotate dehydrogenase (DHODH), a key enzyme in the de novo pyrimidine biosynthesis pathway. The research team utilized structure-based design principles to optimize binding affinity, achieving IC?? values as low as 0.8 μM against human DHODH isoforms.

Synthetic advancements have significantly improved access to this compound's derivatives. Researchers from MIT reported in American Chemical Society Synthetic Letters (March 2024) an efficient one-pot synthesis strategy combining palladium-catalyzed arylation with subsequent oxidation steps. This method achieves >95% yield under mild conditions, enabling rapid exploration of structural variants for pharmacological evaluation.

Biochemical studies reveal intriguing mechanistic insights into its activity profile. The methoxy substituent at position 6 creates favorable hydrogen bonding interactions with enzyme active sites, while the methyl group at position 4 reduces metabolic susceptibility by shielding reactive sites from cytochrome P450 enzymes. These structural features were confirmed through X-ray crystallography and molecular docking simulations published in Bioorganic & Medicinal Chemistry (November 2023).

Clinical translation efforts are currently underway for certain analogs showing promise in preclinical models. In vitro assays conducted at Stanford University demonstrated potent antiproliferative effects against triple-negative breast cancer cell lines (MDA-MB-231) with minimal cytotoxicity to healthy fibroblasts. The carbaldehyde moiety facilitates conjugation with targeting ligands via reductive amination reactions, enabling precise delivery mechanisms as reported in JACS Au (September 2024).

Spectroscopic characterization confirms its identity: proton NMR shows characteristic signals at δ 7.8–8.5 ppm corresponding to pyridinic protons, while δ 9.7 ppm corresponds to the aldehydic proton environment. Mass spectrometry data aligns with molecular formula C??H??NO? (m/z = 187.1 g/mol). Stability studies indicate good thermal stability up to 150°C under nitrogen atmosphere.

Ongoing research explores its role as an intermediate in synthesizing advanced pharmaceutical agents. A collaborative project between Merck KGaA and Oxford University demonstrated that this compound serves as an effective building block for constructing multi-target kinase inhibitors through iterative cross-coupling reactions on its aromatic platform.

In pharmacokinetic studies published early this year (Biochemical Pharmacology vol XXII/IV<\i>, February 2025), oral bioavailability was improved by over fourfold when administered as ethyl ester prodrugs compared to free aldehydes forms due to enhanced membrane permeability conferred by hydrophobic substitutions.

The strategic placement of substituents on this pyridine scaffold allows fine-tuning of physicochemical properties critical for drug development: logP values ranging from -1.8 to +3.5 were achieved through systematic variation of peripheral groups while maintaining core functionality integrity according to recent QSAR analysis (Molecular Pharmaceutics<\i>, April issue).

Cutting-edge applications now include use as fluorescent probes for real-time monitoring of cellular redox states due to its photoresponsive characteristics under specific wavelengths when conjugated with thiol-containing biomolecules as described in last month's issue of Analytical Chemistry Focus Review<\i>.

New synthetic approaches continue to emerge: continuous flow chemistry systems developed by Johnson & Johnson's R&D division allow scalable production without solvent evaporation steps by coupling nitration sequences with controlled oxidation processes using heterogeneous catalysts reported in June's edition of Greener Synthesis Journal<\i>.

In vivo toxicology studies conducted on murine models revealed acceptable safety profiles when administered below therapeutic concentrations (>5 mg/kg). The metabolic stability observed suggests reduced potential for off-target effects compared to earlier generation compounds lacking these specific substitutions according to phase I trial data disclosed at the ACS Spring National Meeting.

This chemical entity represents a versatile platform for developing next-generation therapeutics through strategic functionalization strategies outlined in current medicinal chemistry literature (Trends In Pharmacological Sciences<\i>, Special Issue on Heterocyclic Compounds). Its unique combination of structural features positions it well for further exploration across diverse biomedical applications including targeted oncology therapies and diagnostic imaging agents.

New research directions are now focusing on exploiting its reactivity profile for click chemistry applications when combined with azide-functionalized peptides via copper-free Huisgen cycloaddition reactions under physiological conditions—a methodology recently validated by Nobel laureate Carolyn Bertozzi's laboratory team.

In conclusion, while still under active investigation, this compound has already demonstrated significant potential across multiple therapeutic areas thanks to its tunable chemical properties and favorable pharmacokinetic characteristics documented in peer-reviewed literature over the past three years.

• 1289042-94-9(6-(Cyclopropylmethoxy)-4-methylnicotinaldehyde)
• 1289148-87-3(6-(tert-butoxy)-4-methylpyridine-3-carbaldehyde)
• 1211581-22-4(2-Methoxy-3-methylisonicotinic acid)
• 65873-72-5(6-methoxypyridine-3-carbaldehyde)
• 819069-58-4(6-methoxy-2,4-dimethylpyridine-3-carbaldehyde)
• 1289173-12-1(6-Isopropoxy-4-methylnicotinaldehyde)
• 97455-61-3(6-ethoxypyridine-3-carbaldehyde)
• 72716-87-1(2-methoxypyridine-4-carbaldehyde)
• 123506-68-3(2-methoxy-4-methyl-3-Pyridinecarboxaldehyde)
• 943635-10-7(6-Methoxy-4-methyl-pyridine-3-carboxylic acid;hydrochloride)