7-trifluoromethyl-4-hydroxyquinoline

7-Trifluoromethyl-4-hydroxyquinoline

7-Trifluoromethyl-4-hydroxyquinoline is a chemical compound belonging to the class of quinoline derivatives. It is characterized by the presence of a trifluoromethyl group at the 7-position and a hydroxyl group at the 4-position of the quinoline ring. This compound is of interest in medicinal chemistry due to its potential biological activities and its role as a building block in the synthesis of more complex pharmaceutical agents.

Chemical Structure and Properties

The molecular formula of 7-trifluoromethyl-4-hydroxyquinoline is C₁₀H₆F₃NO. The presence of the trifluoromethyl group (CF₃) imparts unique chemical properties, such as increased lipophilicity and metabolic stability, which can influence the compound's pharmacokinetic profile.

The compound's structure can be described as follows:

• Quinoline Ring: A bicyclic aromatic compound consisting of a benzene ring fused to a pyridine ring.
• 4-Hydroxy Group: A hydroxyl group attached to the fourth carbon of the quinoline ring, contributing to the compound's potential for hydrogen bonding and influencing its solubility.
• 7-Trifluoromethyl Group: A trifluoromethyl group attached to the seventh carbon, known for its electron-withdrawing properties and its ability to enhance the biological activity of the compound.

Synthesis

The synthesis of 7-trifluoromethyl-4-hydroxyquinoline can be achieved through various synthetic routes. One common method involves the cyclization of appropriate aniline derivatives with trifluoroacetic acid derivatives under acidic conditions. The reaction typically proceeds through the formation of an intermediate, which undergoes cyclization to form the quinoline core.

Biological Activity

7-Trifluoromethyl-4-hydroxyquinoline has been studied for its potential biological activities, including antimicrobial, anticancer, and anti-inflammatory effects. The trifluoromethyl group is known to enhance the compound's ability to interact with biological targets, potentially leading to increased efficacy.

Applications

This compound serves as a valuable intermediate in the synthesis of more complex molecules with potential therapeutic applications. Its unique chemical properties make it a useful scaffold for the development of new drugs targeting various diseases.

Also see

• Quinoline
• Trifluoromethyl group
• Medicinal chemistry
• Pharmacokinetics