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• 2. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
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Professional Introduction to 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (CAS No. 1190322-46-3)

3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile, with the chemical identifier CAS No. 1190322-46-3, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the pyrrolopyridine class, a structural motif widely recognized for its biological activity and utility in drug development. The presence of both chloro and nitrile functional groups in its molecular framework imparts unique reactivity, making it a valuable intermediate in synthetic chemistry and a potential candidate for further derivatization to explore novel pharmacological properties.

The pyrrolo[2,3-b]pyridine scaffold is a privileged structure in medicinal chemistry, frequently incorporated into molecules targeting various therapeutic areas such as oncology, neurology, and infectious diseases. Its bicyclic nature provides a rigid core that can be modulated through structural modifications to optimize binding affinity and selectivity. In particular, the 5-carbonitrile substituent enhances the compound's solubility and stability while also serving as a versatile handle for further functionalization via nucleophilic addition or transition-metal-catalyzed reactions.

Recent advancements in drug discovery have highlighted the importance of 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile as a key building block for designing small-molecule inhibitors. For instance, studies have demonstrated its utility in generating derivatives with potent activity against kinases and other enzyme targets implicated in cancer progression. The chloro group, in particular, allows for easy introduction of diverse pharmacophores through palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the construction of complex molecular architectures.

One notable application of this compound is in the synthesis of small-molecule inhibitors targeting protein-protein interactions (PPIs). PPIs are critical mediators of cellular signaling pathways and are often considered "undruggable" targets due to their lack of well-defined binding pockets. However, the rigid pyrrolopyridine core of 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile provides an excellent platform for designing molecules that can disrupt these interactions through induced fit or enthalpic stabilization mechanisms. Recent publications have shown promising results in using derivatives of this compound to inhibit PPIs involved in inflammatory diseases and neurodegenerative disorders.

The nitrile group at the 5-position not only contributes to the compound's chemical diversity but also plays a crucial role in its pharmacokinetic properties. Nitriles are known to exhibit good metabolic stability and can be hydrolyzed to carboxylic acids under physiological conditions, which may enhance drug bioavailability. Additionally, the nitrile functionality can participate in hydrogen bonding interactions with biological targets, further improving binding affinity and selectivity.

In terms of synthetic methodologies, 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile serves as an excellent precursor for constructing more complex heterocycles through cyclocondensation reactions or metal-catalyzed cyclizations. For example, it can be converted into thiazolo[5,4-d]pyrimidines or benzothiazepines via multi-step synthetic routes involving cyclodehydration or nucleophilic aromatic substitution. These transformations expand its utility as a versatile intermediate in combinatorial chemistry libraries and high-throughput screening campaigns.

The growing interest in bioconjugation strategies has also positioned this compound as a valuable reagent for developing probes and therapeutics that require site-specific labeling. The chloro group can be selectively modified using reagents such as trityl chloride or dimethylformamide (DMF) under mild conditions, allowing for the introduction of diverse functional handles including alkynes or azides. These modifications are particularly useful for constructing probes that can be visualized using fluorescence microscopy or incorporated into drug conjugates via click chemistry reactions.

From a computational chemistry perspective, 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile has been extensively studied to understand its interaction with biological targets at the molecular level. Molecular docking simulations have revealed that this compound can bind effectively to active sites of enzymes such as kinases by forming hydrogen bonds with key residues and stacking against aromatic patches on the protein surface. These insights have guided the design of optimized derivatives with enhanced potency and selectivity against specific disease-related targets.

The pharmaceutical industry has recognized the potential of this scaffold due to its versatility and biological relevance. Several companies have included analogs of 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile in their pipeline programs targeting cancer and inflammatory diseases. Early-phase clinical trials have shown encouraging results with some derivatives demonstrating significant therapeutic effects without apparent toxicity at effective doses. These findings underscore the importance of this compound as a lead structure for further development into novel therapeutics.

In conclusion, 3-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (CAS No. 1190322-46-3) is a multifaceted compound with broad applications in pharmaceutical research and drug development. Its unique structural features make it an ideal candidate for generating biologically active molecules through diverse synthetic strategies while offering favorable pharmacokinetic properties when properly optimized. As research continues to uncover new therapeutic targets and innovative drug design paradigms, this compound will undoubtedly remain at forefrontof medicinal chemistry innovation.

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