• 1. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 2. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 3. Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid
  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 4. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212
• 5. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Quinoline carboxylic acids

4-Bromoquinoline-3-carboxylic Acid (CAS No. 1378260-46-8): A Comprehensive Overview

4-Bromoquinoline-3-carboxylic acid (CAS No. 1378260-46-8) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of quinolines, which are known for their diverse biological activities and potential therapeutic applications. In this article, we will delve into the chemical properties, synthesis methods, biological activities, and recent research advancements related to 4-Bromoquinoline-3-carboxylic acid.

Chemical Properties

4-Bromoquinoline-3-carboxylic acid is a white crystalline solid with a molecular formula of C₁₀H₆BrNO₂. It has a molecular weight of 250.07 g/mol and is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF). The compound exhibits strong UV absorption and can be detected using various spectroscopic techniques, including UV-Vis, IR, and NMR spectroscopy. The presence of the bromine atom and the carboxylic acid group imparts unique reactivity and functional properties to the molecule.

Synthesis Methods

The synthesis of 4-Bromoquinoline-3-carboxylic acid can be achieved through several routes, each with its own advantages and limitations. One common method involves the bromination of quinoline followed by carboxylation. For instance, 4-bromoquinoline can be synthesized by brominating quinoline with bromine or N-bromosuccinimide (NBS) in an appropriate solvent such as acetic acid or dichloromethane. Subsequently, the carboxylation step can be performed using various reagents, such as potassium permanganate or chloroacetic acid in an alkaline medium.

An alternative approach involves the condensation of 4-bromoaniline with ethyl acetoacetate followed by cyclization to form the quinoline ring. This method is particularly useful for preparing substituted quinolines with specific functional groups. Recent advancements in green chemistry have also led to the development of more environmentally friendly synthesis methods, such as using microwave-assisted reactions or catalytic systems to improve yield and reduce waste.

Biological Activities

4-Bromoquinoline-3-carboxylic acid has been extensively studied for its biological activities, particularly in the context of its potential therapeutic applications. One of the key areas of interest is its antiproliferative activity against various cancer cell lines. Research has shown that this compound can inhibit the growth of cancer cells by inducing apoptosis and cell cycle arrest. For example, a study published in the Journal of Medicinal Chemistry demonstrated that 4-Bromoquinoline-3-carboxylic acid effectively inhibited the proliferation of human breast cancer cells (MCF-7) by targeting key signaling pathways involved in cell survival and proliferation.

In addition to its antiproliferative effects, 4-Bromoquinoline-3-carboxylic acid has also been investigated for its anti-inflammatory properties. Inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease are characterized by chronic inflammation, which can lead to tissue damage and organ dysfunction. Studies have shown that this compound can modulate the expression of pro-inflammatory cytokines and enzymes, thereby reducing inflammation and associated symptoms.

Clinical Applications and Research Advancements

The potential clinical applications of 4-Bromoquinoline-3-carboxylic acid are currently being explored through preclinical studies and early-stage clinical trials. One promising area is its use as a lead compound for developing novel anticancer drugs. Researchers are focusing on optimizing the structure of this compound to enhance its potency and selectivity while minimizing toxicity. For instance, a recent study published in Cancer Research reported that a derivative of 4-Bromoquinoline-3-carboxylic acid, modified with a hydroxyl group at the 5-position, exhibited enhanced antitumor activity against colorectal cancer cells both in vitro and in vivo.

Beyond cancer therapy, there is growing interest in exploring the potential of 4-Bromoquinoline-3-carboxylic acid for treating other diseases characterized by dysregulated cellular processes. For example, neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease involve abnormal protein aggregation and oxidative stress. Preliminary studies have shown that this compound can protect neurons from oxidative damage and promote neurogenesis, suggesting its potential as a neuroprotective agent.

Safety Considerations and Future Directions

The safety profile of 4-Bromoquinoline-3-carboxylic acid is an important consideration for its development as a therapeutic agent. Preclinical studies have generally shown that this compound is well-tolerated at therapeutic doses, with minimal toxicity observed in animal models. However, further research is needed to fully evaluate its safety in humans, particularly regarding long-term use.

In conclusion, 4-Bromoquinoline-3-carboxylic acid (CAS No. 1378260-46-8) is a promising compound with diverse biological activities and potential therapeutic applications. Ongoing research continues to uncover new insights into its mechanisms of action and optimize its structure for improved efficacy and safety. As our understanding of this compound deepens, it holds great promise for advancing medical treatments in various fields.

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