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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Furans Furoic acids
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Furans Furoic acid and derivatives Furoic acids

5-(2,4-Dichlorophenyl)furan-2-carboxylic Acid (CAS No. 134448-46-7): An Overview of Its Structure, Properties, and Applications in Medicinal Chemistry

5-(2,4-Dichlorophenyl)furan-2-carboxylic acid (CAS No. 134448-46-7) is a versatile compound that has garnered significant attention in the field of medicinal chemistry due to its unique structural features and potential biological activities. This compound belongs to the class of furan-2-carboxylic acids, which are characterized by a furan ring substituted with a carboxylic acid group. The presence of the dichlorophenyl substituent at the 5-position of the furan ring imparts additional chemical and biological properties that make it an interesting target for various applications.

The molecular formula of 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid is C₁₁H₆Cl₂O₃, and its molecular weight is approximately 253.07 g/mol. The compound exhibits a planar structure with the furan ring and the dichlorophenyl group lying in the same plane, which can influence its interactions with biological targets. The carboxylic acid group provides the molecule with acidic properties, making it suitable for various chemical reactions and biological assays.

In recent years, 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid has been studied extensively for its potential as a lead compound in drug discovery. One of the key areas of interest is its anti-inflammatory activity. Research has shown that this compound can inhibit the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α) in vitro. These findings suggest that 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid could be a valuable candidate for the development of new anti-inflammatory drugs.

Beyond its anti-inflammatory properties, 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid has also been investigated for its potential anticancer effects. Studies have demonstrated that this compound can induce apoptosis in various cancer cell lines, including breast cancer and colorectal cancer cells. The mechanism of action appears to involve the modulation of signaling pathways such as p53 and Bcl-2, which are crucial for cell survival and death. These findings highlight the potential of 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid as a lead compound for anticancer drug development.

The synthesis of 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid has been optimized using various methodologies to improve yield and purity. One common approach involves the reaction of 2,4-dichlorobenzaldehyde with furfuryl alcohol followed by oxidation to form the carboxylic acid group. This synthetic route is efficient and scalable, making it suitable for large-scale production in industrial settings.

In addition to its therapeutic applications, 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid has also been explored as a building block for the synthesis of more complex molecules. Its reactivity and functional groups make it an excellent starting material for derivatization reactions, allowing chemists to introduce additional functionalities that can enhance or modify its biological activities. For example, esterification or amide formation can be used to create prodrugs or analogs with improved pharmacokinetic properties.

The solubility and stability of 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid are important considerations for its use in pharmaceutical formulations. While it is generally stable under standard laboratory conditions, care should be taken to avoid exposure to strong acids or bases that could degrade the molecule. Solubility studies have shown that this compound has limited solubility in water but is more soluble in organic solvents such as dimethyl sulfoxide (DMSO) or dimethylformamide (DMF). These properties can influence its bioavailability and formulation strategies.

To further understand the biological activities of 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid, researchers have employed various in vitro and in vivo models. In vitro studies using cell cultures have provided insights into its mechanisms of action at the molecular level, while in vivo studies using animal models have evaluated its efficacy and safety profiles. These comprehensive approaches have helped to validate its potential as a therapeutic agent.

In conclusion, 5-(2,4-Dichlorophenyl)furan-2-carboxylic acid (CAS No. 134448-46-7) is a promising compound with diverse applications in medicinal chemistry. Its unique structural features and biological activities make it an attractive target for drug discovery and development. Ongoing research continues to uncover new aspects of its potential therapeutic uses, further solidifying its importance in the field.

• 186830-98-8(5-(2 5-DICHLOROPHENYL)-2-FUROIC ACID 9&)
• 55462-54-9(5-(2,3-dichlorophenyl)furan-2-carboxylic acid)
• 41019-43-6(5-(2-Chlorophenyl)furan-2-carboxylic acid)
• 41019-45-8(5-(4-Chlorophenyl)furan-2-carboxylic acid)
• 56300-69-7(5-(2,4-Dichlorophenyl)furan-2-carbaldehyde)
• 41019-44-7(5-(3-Chlorophenyl)-2-furoic Acid)
• 54023-01-7(5-(3,4-Dichlorophenyl)-2-furoic Acid)
• 480423-60-7( )
• 355142-36-8(2-Chloro-5-(5-formylfuran-2-yl)benzoic acid)
• 302911-88-2(5-2-Chloro-5-(trifluoromethyl)phenylfuran-2-carboxylic Acid)