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  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
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  Denis V. Korchagin,Elena A. Yureva,Alexander V. Akimov,Eugenii Ya. Misochko,Gennady V. Shilov,Artem D. Talantsev,Roman B. Morgunov,Alexander A. Shakin,Sergey M. Aldoshin,Boris S. Tsukerblat Dalton Trans., 2017,46, 7540-7548
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Para cresols
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Cresols Para cresols

Introduction to 2-(5-isoxazolyl)-4-methylphenol (CAS No. 164171-56-6)

2-(5-isoxazolyl)-4-methylphenol, identified by its Chemical Abstracts Service (CAS) number 164171-56-6, is a significant compound in the realm of pharmaceutical chemistry and bioorganic synthesis. This heterocyclic aromatic molecule has garnered attention due to its unique structural features and potential applications in medicinal chemistry. The presence of both an isoxazole ring and a methylphenol moiety endows it with distinct chemical properties that make it a valuable scaffold for drug discovery and development.

The compound’s structure consists of a benzene ring substituted with a hydroxyl group at the 4-position and an isoxazole ring fused to the 5-position of the benzene core. The isoxazole ring, characterized by its three-membered oxygen-containing heterocycle, contributes to the molecule’s reactivity and biological activity. This structural motif is well-documented for its role in various pharmacophores, particularly in antimicrobial, anti-inflammatory, and anticancer agents.

In recent years, there has been a surge in research focusing on the development of novel therapeutic agents derived from isoxazole-containing compounds. The combination of the aromatic methylphenol group with the isoxazole moiety in 2-(5-isoxazolyl)-4-methylphenol suggests potential interactions with biological targets such as enzymes and receptors. This dual functionality makes it an attractive candidate for further exploration in drug design.

One of the most compelling aspects of this compound is its potential as a precursor for synthesizing more complex derivatives. Researchers have leveraged its structural framework to develop molecules with enhanced pharmacological properties. For instance, modifications at the hydroxyl or methyl substituents can lead to variations in solubility, metabolic stability, and target specificity. Such flexibility underscores the importance of 2-(5-isoxazolyl)-4-methylphenol as a building block in medicinal chemistry.

The pharmaceutical industry has increasingly recognized the importance of heterocyclic compounds in drug development. Isoxazole derivatives, in particular, have shown promise in several therapeutic areas. Studies have demonstrated that these compounds can exhibit inhibitory effects on various enzymes involved in disease pathways. For example, derivatives of isoxazole have been investigated for their potential to modulate inflammatory responses by inhibiting key enzymes such as cyclooxygenase (COX) or lipoxygenase (LOX).

Moreover, the aromatic methylphenol moiety in 2-(5-isoxazolyl)-4-methylphenol contributes to its ability to engage with biological targets through hydrophobic interactions and hydrogen bonding. This dual mode of interaction enhances its binding affinity and selectivity towards specific biological receptors. Such characteristics are crucial for developing drugs that can effectively interact with their targets while minimizing off-target effects.

Recent advancements in computational chemistry have further accelerated the discovery process for novel drug candidates like 2-(5-isoxazolyl)-4-methylphenol. Molecular modeling techniques allow researchers to predict the binding affinity and mode of interaction between this compound and potential biological targets. These simulations provide valuable insights into how structural modifications can optimize pharmacological activity, guiding experimental design and accelerating the development pipeline.

In addition to its pharmaceutical applications, 2-(5-isoxazolyl)-4-methylphenol has shown promise in other areas of chemical research. Its unique reactivity makes it a useful intermediate in organic synthesis, enabling the construction of more complex molecular architectures. Researchers have explored its use in cross-coupling reactions, which are fundamental to constructing biaryl systems found in many bioactive molecules.

The synthesis of 2-(5-isoxazolyl)-4-methylphenol involves multi-step organic transformations that highlight its synthetic utility. The introduction of the isoxazole ring typically requires cyclization reactions under controlled conditions, while functionalization at the phenolic position can be achieved through various electrophilic or nucleophilic substitution methods. These synthetic strategies underscore the compound’s versatility as a chemical building block.

From a broader perspective, the study of compounds like 2-(5-isoxazolyl)-4-methylphenol contributes to our understanding of structure-activity relationships (SAR) in medicinal chemistry. By analyzing how structural changes affect biological activity, researchers can gain insights into molecular recognition processes and develop more rational approaches to drug design. This knowledge is essential for accelerating the discovery of new therapeutic agents that address unmet medical needs.

The growing interest in natural product-inspired scaffolds has also influenced research on 2-(5-isoxazolyl)-4-methylphenol. Many bioactive compounds isolated from plants or microorganisms feature similar structural motifs, suggesting that they may share common biosynthetic origins. By studying synthetic analogs like this compound, researchers can gain insights into natural product biosynthesis and identify new leads for drug development.

In conclusion,2-(5-isoxazolyl)-4-methylphenol (CAS No. 164171-56-6) represents a promising compound with diverse applications in pharmaceutical chemistry and organic synthesis. Its unique structural features make it a valuable scaffold for drug discovery, offering opportunities for developing novel therapeutic agents with enhanced pharmacological properties. As research continues to uncover new applications for this compound, it will undoubtedly remain a key player in advancing chemical biology and medicinal chemistry.

• 67363-57-9(Phenol, 2-(4-methyl-5-isoxazolyl)-)
• 391927-01-8(3-(Isoxazol-5-yl)phenol)
• 61348-47-8(2-(5-Isoxazolyl)phenol)
• 288844-43-9(Phenol,2-(5-isoxazolyl)-4,6-dimethyl-)
• 288844-44-0(Phenol,2-(5-isoxazolyl)-4-(1-methylethyl)-)
• 104516-57-6(Phenol,2-(5-isoxazolyl)-4-methyl-)
• 3672-48-8(5-(4-Methoxyphenyl)isoxazole)
• 213690-27-8(4-Bromo-2-(isoxazol-5-yl)phenol)
• 288401-62-7(5-(5-Fluoro-2-hydroxyphenyl)isoxazole)
• 86176-56-9(4-Chloro-2-(isoxazol-5-yl)phenol)