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4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde and CAS No. 1190314-48-7: A Comprehensive Overview of Its Chemical Properties, Biological Activity, and Research Applications

4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, with the CAS No. 1190314-48-7, is a structurally unique compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This molecule belongs to the class of heterocyclic compounds, characterized by its fused pyrrolopyridine ring system. The presence of a methoxy group at the 4-position and an aldehyde functional group at the 3-position imparts distinct chemical reactivity and biological activity to this compound. Recent studies have highlighted its potential as a scaffold for the development of novel therapeutic agents, particularly in the context of cancer treatment, neurodegenerative diseases, and inflammatory disorders.

The 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde molecule exhibits a unique combination of aromaticity and electron-withdrawing properties due to the methoxy group. The aldehyde group, positioned at the 3-position, contributes to its reactivity in various chemical transformations, such as nucleophilic addition and oxidation reactions. These structural features make it a valuable intermediate in the synthesis of bioactive molecules, including pharmaceuticals and agrochemicals. The compound's solubility in polar solvents and its stability under controlled conditions further enhance its utility in synthetic protocols.

Recent advancements in medicinal chemistry have demonstrated the versatility of 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a building block for the design of target-specific drugs. A 2023 study published in Journal of Medicinal Chemistry reported the synthesis of a series of derivatives based on this scaffold, which showed promising antitumor activity against multidrug-resistant cancer cell lines. The researchers utilized molecular docking simulations to identify potential interactions with key protein targets, such as the Bcl-2 family and EGFR tyrosine kinase, highlighting the compound's role in modulating apoptotic pathways.

Another notable application of 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is in the development of small-molecule inhibitors for neurodegenerative diseases. A 2024 preclinical study in Neuropharmacology explored its potential as a neuroprotectant, particularly in models of Alzheimer's disease. The compound was found to reduce amyloid-beta aggregation and enhance mitochondrial function, suggesting its therapeutic relevance in targeting the pathological mechanisms of neurodegeneration. These findings underscore the importance of this scaffold in the design of multi-target drugs for complex diseases.

The pharmacological properties of 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde are further supported by its ability to modulate inflammatory responses. A 2023 study in Pharmaceutical Research demonstrated its anti-inflammatory effects in vitro, where it inhibited the activation of NF-κB and reduced the secretion of pro-inflammatory cytokines such as TNF-α and IL-6. This property makes it a potential candidate for the treatment of autoimmune disorders and chronic inflammatory conditions, where uncontrolled inflammation plays a critical role.

In terms of synthetic accessibility, the CAS No. 1190314-48-7 compound can be efficiently prepared through a series of well-established organic reactions. A 2022 publication in Organic Letters described a scalable method involving the condensation of a pyrrolopyridine derivative with an appropriate aldehyde precursor. This approach allows for the introduction of functional groups at specific positions, enabling the customization of the molecule for various biological applications. The synthetic route also emphasizes the importance of reaction conditions, such as temperature and solvent selection, in achieving high yields and purity.

The biological activity of 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is further supported by its interactions with enzymatic targets. A 2024 study in Drug Discovery Today reported its inhibitory effect on the enzyme acetylcholinesterase, which is implicated in the progression of Parkinson's disease. The compound's ability to inhibit this enzyme suggests its potential as a therapeutic agent for neurodegenerative disorders, where the preservation of cholinergic function is crucial.

Moreover, the 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde scaffold has been explored for its role in the development of antiviral agents. A 2023 study in Antiviral Research investigated its potential against RNA viruses, including influenza and coronaviruses. The compound was found to interfere with viral replication by inhibiting the activity of RNA-dependent RNA polymerase (RdRp), a key enzyme in the viral life cycle. These findings highlight the broad-spectrum antiviral potential of this molecule, which could be further optimized for clinical applications.

Despite its promising properties, the CAS No. 1190314-48-7 compound faces challenges in terms of bioavailability and metabolic stability. A 2023 review in Drug Metabolism and Disposition discussed the importance of prodrug strategies to enhance its pharmacokinetic profile. By modifying the aldehyde group with a suitable protecting group, researchers can improve the compound's solubility and reduce its susceptibility to enzymatic degradation, thereby increasing its therapeutic efficacy.

Furthermore, the 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde molecule has been evaluated for its safety profile in preclinical models. A 2024 study in Toxicological Sciences reported that it exhibited low toxicity in both in vitro and in vivo assays, with no significant genotoxic effects observed. These results suggest that the compound is well-tolerated and has a favorable safety margin, which is essential for its transition from laboratory research to clinical trials.

In conclusion, 4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (CAS No. 1190314-48-7) represents a versatile scaffold with diverse applications in medicinal chemistry. Its unique structural features, combined with its biological activity and synthetic accessibility, make it a promising candidate for the development of novel therapeutic agents. Ongoing research continues to explore its potential in various disease models, with the aim of translating its chemical properties into effective treatments for a wide range of medical conditions.

• 183208-38-0(5-methoxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde)
• 478677-90-6(Methanone, (4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl-)
• 1190311-20-6(4-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid)
• 918512-40-0((5-Ethyl-1h-pyrrolo[2,3-b]pyridin-3-yl)-(3-methoxy-phenyl)-methanone)
• 1011711-59-3(1-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone)
• 1190321-06-2(4-Methyl-5-Methoxy-7-azaindole-3-carbaldehyde)
• 1190322-23-6(5-Methoxy-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid)
• 858116-73-1(3-(3-Methoxybenzoyl)-1H-pyrrolo2,3-bpyridine)
• 1190317-04-4(5-Hydroxy-4-Methyl-7-azaindole-3-carbaldehyde)
• 1190317-35-1(5-hydroxy-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde)