4-hydroxyquinoline-3-carboxylic acid

4-Hydroxyquinoline-3-carboxylic acid is an organic compound that belongs to the class of quinoline derivatives. It is characterized by a quinoline core structure with a hydroxyl group at the 4-position and a carboxylic acid group at the 3-position. This compound is of interest in the field of medicinal chemistry due to its potential biological activities and its role as a building block in the synthesis of more complex molecules.

Chemical Structure and Properties

The molecular formula of 4-hydroxyquinoline-3-carboxylic acid is C₁₀H₇NO₃. It has a molecular weight of 189.17 g/mol. The structure consists of a bicyclic aromatic system, which is a fusion of a benzene ring and a pyridine ring, forming the quinoline backbone. The presence of the hydroxyl and carboxylic acid groups imparts unique chemical properties, such as the ability to form hydrogen bonds and participate in acid-base reactions.

Synthesis

The synthesis of 4-hydroxyquinoline-3-carboxylic acid can be achieved through various methods. One common approach involves the cyclization of an appropriate aniline derivative with a β-ketoester, followed by oxidation and hydrolysis steps. The choice of starting materials and reaction conditions can influence the yield and purity of the final product.

Biological Activity

4-Hydroxyquinoline-3-carboxylic acid and its derivatives have been studied for their potential antimicrobial, antiviral, and anticancer activities. The compound's ability to chelate metal ions and interact with biological targets makes it a candidate for drug development. Research is ongoing to explore its mechanism of action and optimize its pharmacological properties.

Applications

In addition to its potential therapeutic uses, 4-hydroxyquinoline-3-carboxylic acid is used as an intermediate in the synthesis of dyes, pigments, and other organic compounds. Its derivatives are also employed in the development of coordination complexes for use in catalysis and material science.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 4-hydroxyquinoline-3-carboxylic acid. It should be stored in a cool, dry place, and protective equipment such as gloves and goggles should be worn to prevent skin and eye contact.

Also see

• Quinoline
• Carboxylic acid
• Hydroxyl group
• Medicinal chemistry