6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid

6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid is a synthetic organic compound that belongs to the class of quinoline derivatives. This compound is of interest in the field of medicinal chemistry due to its potential biological activities and applications in drug development.

Chemical Structure and Properties

6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid is characterized by a quinoline core structure with a phenylstyryl group at the 6-position and carboxylic acid groups at the 2 and 4 positions. The presence of the phenylstyryl moiety contributes to its unique chemical properties, including its ability to participate in π-π stacking interactions and potential fluorescence.

Molecular Formula

The molecular formula of 6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid is C₂₆H₁₇NO₄.

Molecular Weight

The molecular weight of this compound is approximately 407.42 g/mol.

Physical Properties

This compound typically appears as a crystalline solid. It is sparingly soluble in water but may be soluble in organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF).

Synthesis

The synthesis of 6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid can be achieved through a multi-step organic synthesis process. A common approach involves the condensation of a suitable quinoline derivative with a phenylstyryl precursor, followed by functional group transformations to introduce the carboxylic acid groups.

Biological Activity

Research into the biological activity of 6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid is ongoing. Preliminary studies suggest that it may exhibit activity against certain cancer cell lines, potentially through mechanisms involving DNA intercalation or inhibition of specific enzymes. Further studies are required to elucidate its mode of action and therapeutic potential.

Applications

Due to its structural features, 6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid is being investigated for its potential use as a fluorescent probe in biological imaging. Its ability to bind to nucleic acids and proteins could make it a valuable tool in the study of cellular processes.

Safety and Handling

As with many chemical compounds, appropriate safety measures should be taken when handling 6-(4'-Phenylstyryl)-quinoline-2,4-dicarboxylic acid. It should be handled in a well-ventilated laboratory setting, with the use of personal protective equipment such as gloves and goggles.

Also see

• Quinoline
• Carboxylic acid
• Fluorescent probe
• Medicinal chemistry