Production Method 1

923169-37-3

Reaction Conditions

Reference

Preparation of oxazinoquinoline compounds as stimulator of interferon genes (STING) modulators, and compositions and methods thereof

, World Intellectual Property Organization, , ,

Production Method 2

117423-43-5

923169-37-3

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  2 h, 90 °C; 90 °C → rt
1.2 Solvents: Water ;  pH 4 - 5, rt

Reference

Preparation of imidazolidines as matrix metalloproteinase (MMP) inhibitors useful in treatment of diseases

, World Intellectual Property Organization, , ,

4-(Hydroxymethyl)pyridine-2-carboxylic acid Raw materials

• 4-((Tert-butyldimethylsilyloxy)methyl)picolinonitrile

4-(Hydroxymethyl)pyridine-2-carboxylic acid Preparation Products

• 4-(Hydroxymethyl)pyridine-2-carboxylic acid (923169-37-3)

• 1. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
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• 4. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 5. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Pyridinecarboxylic acids

Introduction to 4-(Hydroxymethyl)pyridine-2-carboxylic acid (CAS No. 923169-37-3)

4-(Hydroxymethyl)pyridine-2-carboxylic acid, identified by the Chemical Abstracts Service Number (CAS No.) 923169-37-3, is a significant compound in the realm of chemical and pharmaceutical research. This heterocyclic carboxylic acid derivative features a pyridine core substituted with both a hydroxymethyl group at the 4-position and a carboxylic acid moiety at the 2-position. Its unique structural configuration makes it a valuable intermediate in synthetic chemistry, particularly in the development of bioactive molecules.

The compound's molecular structure, characterized by the presence of both oxygen-rich functional groups and a nitrogen-containing heterocycle, positions it as a versatile building block for medicinal chemistry applications. The hydroxymethyl (-CH?OH) group introduces reactivity suitable for further functionalization, while the carboxylic acid (-COOH) group provides opportunities for amide bond formation, esterification, or salt formation, enhancing its utility in drug synthesis.

In recent years, 4-(Hydroxymethyl)pyridine-2-carboxylic acid has garnered attention in the pharmaceutical industry due to its potential role in designing novel therapeutic agents. Its pyridine scaffold is a common motif in many biologically active compounds, including antiviral, antibacterial, and anticancer agents. The incorporation of this scaffold into drug candidates often enhances binding affinity to biological targets, making it a preferred choice for medicinal chemists.

One of the most compelling aspects of 4-(Hydroxymethyl)pyridine-2-carboxylic acid is its role as a precursor in the synthesis of more complex molecules. For instance, researchers have explored its use in constructing pyridine-based peptidomimetics, which mimic the structure and function of natural peptides while avoiding their limitations such as degradation and immunogenicity. These peptidomimetics have shown promise in targeting various diseases, including cancer and neurodegenerative disorders.

Recent studies have also highlighted the compound's utility in developing small-molecule inhibitors targeting enzyme-catalyzed reactions. The hydroxymethyl group serves as a nucleophilic site for transition-metal-catalyzed cross-coupling reactions, enabling the introduction of diverse substituents at strategic positions within the molecule. This flexibility has been exploited to create libraries of compounds for high-throughput screening (HTS), facilitating the discovery of lead compounds with desired pharmacological properties.

The pharmaceutical industry's interest in 4-(Hydroxymethyl)pyridine-2-carboxylic acid extends to its potential applications in drug delivery systems. Its ability to form stable complexes with other molecules makes it an excellent candidate for encapsulating bioactive agents, improving their stability and bioavailability. Additionally, its solubility characteristics can be tailored through salt formation or derivatization, making it suitable for various administration routes.

In academic research, 4-(Hydroxymethyl)pyridine-2-carboxylic acid has been employed in studying enzyme inhibition mechanisms. Its structural features allow it to mimic substrates or transition states of enzymes, providing insights into catalytic processes and aiding in the design of more effective inhibitors. Such studies are crucial for developing targeted therapies with minimal side effects.

The compound's role in material science is another emerging area of interest. Researchers have investigated its use in creating functional polymers and coatings with enhanced thermal stability and mechanical properties. The pyridine ring contributes to hydrogen bonding networks within polymers, improving their structural integrity and resistance to environmental stressors.

The synthesis of 4-(Hydroxymethyl)pyridine-2-carboxylic acid itself presents an interesting challenge due to its multiple reactive sites. Common synthetic routes involve multi-step organic transformations starting from readily available pyridine derivatives. Advances in catalytic methods have enabled more efficient and sustainable production processes, reducing waste and energy consumption.

Future directions for research on 4-(Hydroxymethyl)pyridine-2-carboxylic acid include exploring its applications in green chemistry initiatives. Researchers are increasingly focusing on developing synthetic pathways that minimize hazardous byproducts and employ renewable feedstocks. The compound's versatility makes it an ideal candidate for such innovations.

The broader impact of 4-(Hydroxymethyl)pyridine-2-carboxylic acid on science and industry underscores its importance as a foundational chemical entity. Its contributions span multiple disciplines, from drug discovery to advanced materials, demonstrating its far-reaching utility. As research continues to uncover new applications for this compound, its significance is likely to grow even further.

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