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2-(2-Hydroxyphenyl)-5-hydroxypyridine: A Comprehensive Overview

2-(2-Hydroxyphenyl)-5-hydroxypyridine (CAS No. 1261970-09-5) is a compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research due to its unique structural properties and potential biological activities. This article aims to provide a comprehensive overview of 2-(2-Hydroxyphenyl)-5-hydroxypyridine, including its chemical structure, synthesis methods, biological activities, and recent research advancements.

Chemical Structure and Properties

2-(2-Hydroxyphenyl)-5-hydroxypyridine is a heterocyclic compound characterized by a pyridine ring substituted with a hydroxyphenyl group at the 2-position and a hydroxyl group at the 5-position. The presence of these functional groups imparts unique chemical and physical properties to the molecule. The hydroxyphenyl group enhances the compound's solubility in polar solvents, while the hydroxyl group on the pyridine ring can participate in hydrogen bonding, influencing its reactivity and biological interactions.

The molecular formula of 2-(2-Hydroxyphenyl)-5-hydroxypyridine is C₁₁H₉NO₃, with a molecular weight of approximately 199.19 g/mol. The compound exists as a white crystalline solid at room temperature and has a melting point of around 180-183°C. Its UV-Vis spectrum shows characteristic absorption bands, which are useful for its identification and quantification in analytical methods.

Synthesis Methods

The synthesis of 2-(2-Hydroxyphenyl)-5-hydroxypyridine has been reported using various methodologies, each with its own advantages and limitations. One common approach involves the condensation of 2-hydroxybenzaldehyde with 5-hydroxypyridine-3-carbaldehyde followed by cyclization. This method typically yields high purity products but may require careful control of reaction conditions to avoid side reactions.

An alternative synthetic route involves the reaction of 2-hydroxybenzaldehyde with 5-hydroxypyridine-3-carbonitrile, followed by reduction to form the final product. This method is advantageous due to its simplicity and higher yield, making it suitable for large-scale production.

Biological Activities

2-(2-Hydroxyphenyl)-5-hydroxypyridine has been studied for its potential biological activities, including antioxidant, anti-inflammatory, and neuroprotective properties. Recent research has shown that this compound exhibits strong antioxidant activity, as evidenced by its ability to scavenge free radicals and inhibit lipid peroxidation. These properties make it a promising candidate for the development of therapeutic agents targeting oxidative stress-related diseases.

In addition to its antioxidant activity, 2-(2-Hydroxyphenyl)-5-hydroxypyridine has demonstrated anti-inflammatory effects in both in vitro and in vivo models. Studies have shown that it can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6, suggesting its potential use in treating inflammatory disorders.

Furthermore, preliminary studies have indicated that 2-(2-Hydroxyphenyl)-5-hydroxypyridine possesses neuroprotective properties. It has been shown to protect neuronal cells from oxidative damage and reduce apoptosis induced by various neurotoxic agents. These findings suggest that the compound may have therapeutic potential in neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.

Clinical Applications and Future Research Directions

The potential clinical applications of 2-(2-Hydroxyphenyl)-5-hydroxypyridine are currently being explored through preclinical studies and early-stage clinical trials. Initial results are promising, but further research is needed to fully understand its safety profile, pharmacokinetics, and efficacy in human subjects.

Ongoing studies are focusing on optimizing the delivery methods and formulations of 2-(2-Hydroxyphenyl)-5-hydroxypyridine to enhance its bioavailability and therapeutic effects. Additionally, efforts are being made to identify novel derivatives with improved pharmacological properties.

In conclusion, 2-(2-Hydroxyphenyl)-5-hydroxypyridine (CAS No. 1261970-09-5) is a multifaceted compound with significant potential in various therapeutic areas. Its unique chemical structure and diverse biological activities make it an attractive target for further research and development in medicinal chemistry and pharmaceutical sciences.

• 3308-02-9(2-Phenylpyridin-3-ol)
• 22912-38-5([2,4'-Bipyridin]-3'-ol, 2',6'-dimethyl-)
• 33421-36-2(2-(Pyridin-2-yl)phenol)
• 76162-93-1([2,4'-Bipyridin]-3'-ol, 6'-phenyl-)
• 1255638-05-1(6-(2-Methoxy-5-methylphenyl)pyridin-3-ol)
• 144190-35-2(2-(2-Hydroxyphenyl)-3-hydroxypyridine)
• 1255638-36-8(6-(2-Methoxyphenyl)pyridin-3-ol)
• 76162-92-0([2,4'-Bipyridin]-3'-ol, 2'-methyl-)
• 1261940-75-3(2-(3,5-Dimethylphenyl)-3-hydroxypyridine)
• 1261940-34-4(2-(3-Methylphenyl)pyridin-3-ol)