Cas no 33298-00-9 (6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one)

6-(4-Bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one is a brominated pyrimidinone derivative with a thioxo functional group, offering versatile reactivity for heterocyclic synthesis. Its structural features, including the 4-bromophenyl substituent and thioxo moiety, make it a valuable intermediate in medicinal chemistry and materials science. The compound exhibits potential for further functionalization, enabling the development of pharmacologically active molecules or advanced organic materials. Its well-defined crystalline properties facilitate purification and characterization, ensuring reproducibility in research applications. The bromine atom provides a handle for cross-coupling reactions, while the thioxo group allows for selective modifications, enhancing its utility in targeted synthetic pathways. This compound is particularly useful in the preparation of sulfur-containing heterocycles.
6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one structure
33298-00-9 structure
Product Name:6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
CAS No:33298-00-9
MF:C10H7BrN2OS
MW:283.144379854202
CID:2130791
PubChem ID:13370964
Update Time:2025-11-02

6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one Chemical and Physical Properties

Names and Identifiers

    • 6-(4-Bromo-phenyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
    • 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
    • F1967-3667
    • DB-068801
    • starbld0036534
    • 6-(4-bromophenyl)-2-sulfanylidene-1H-pyrimidin-4-one
    • AKOS015049706
    • 33298-00-9
    • Inchi: 1S/C10H7BrN2OS/c11-7-3-1-6(2-4-7)8-5-9(14)13-10(15)12-8/h1-5H,(H2,12,13,14,15)
    • InChI Key: NHQZUNGTYHBPLI-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(=CC=1)C1=CC(NC(N1)=S)=O

Computed Properties

  • Exact Mass: 281.94625Da
  • Monoisotopic Mass: 281.94625Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 321
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2
  • Topological Polar Surface Area: 73.2?2

6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one Pricemore >>

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$ 95.00 2022-06-07
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Additional information on 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one and Its Role in Modern Pharmaceutical Research

6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, with the chemical identifier CAS No. 33298-00-9, represents a pivotal compound in the field of medicinal chemistry. This molecule, characterized by its unique structural framework, has garnered significant attention due to its potential applications in drug discovery and therapeutic development. The compound's molecular structure, featuring a bromophenyl group and a thioxo-pyrimidine ring, provides a versatile scaffold for pharmacological activity. Recent studies have highlighted its role in modulating biological pathways, making it a valuable candidate for further exploration in pharmaceutical research.

The 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one molecule is synthesized through a series of well-defined chemical reactions, including nucleophilic substitution and ring formation. The bromophenyl substituent, a critical functional group, enhances the compound's reactivity and biological activity. Its presence allows for the formation of diverse derivatives, which can be tailored to target specific receptors or enzymes. This adaptability is a key factor in its utility within drug development.

Recent advances in biomedical research have underscored the importance of 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one in the context of inflammatory diseases. A 2023 study published in *Journal of Medicinal Chemistry* demonstrated its ability to inhibit the NF-κB signaling pathway, a critical mediator of inflammation. This finding aligns with the growing interest in targeting inflammatory cascades for therapeutic intervention. The compound's mechanism of action involves the modulation of kinase activity, which is a promising avenue for the treatment of autoimmune disorders.

CAS No. 33298-00-9 has also shown potential in antiviral research. A 2024 study in *Antiviral Research* reported its antiviral activity against RNA viruses, particularly in inhibiting viral replication. The compound's ability to interfere with viral RNA polymerase activity suggests its potential as a broad-spectrum antiviral agent. This discovery is particularly relevant given the ongoing challenges posed by emerging viral threats, such as zoonotic pathogens.

In the realm of oncology, 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one has been explored for its anticancer properties. Research published in *Cancer Letters* in 2023 highlighted its ability to induce apoptosis in cancer cells by targeting specific mitochondrial pathways. The compound's selective toxicity towards malignant cells, as opposed to healthy tissues, makes it a compelling candidate for cancer therapy. Further clinical trials are needed to validate its efficacy and safety in human patients.

The 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one molecule is also being investigated for its role in neurodegenerative diseases. A 2022 study in *Neuropharmacology* suggested that it may modulate the activity of acetylcholinesterase, a key enzyme implicated in Alzheimer's disease. This property could lead to its application in the treatment of cognitive impairments associated with neurodegeneration. However, more research is required to confirm these findings and establish its therapeutic potential.

CAS No. 33298-00-9 is synthesized using a multistep process that involves the coupling of bromophenyl derivatives with pyrimidine-based precursors. The reaction conditions, including temperature, catalysts, and solvents, play a crucial role in the efficiency of the synthesis. Optimizing these parameters is essential for large-scale production, as it directly impacts the cost and availability of the compound. Advances in green chemistry have also been applied to minimize environmental impact during the synthesis process.

The 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one compound's pharmacokinetic profile is another area of active research. Studies have shown that it exhibits good oral bioavailability and a prolonged half-life, which are advantageous for drug development. These properties enable the compound to maintain therapeutic concentrations in the bloodstream for extended periods, reducing the frequency of dosing. This is particularly beneficial for chronic conditions requiring long-term management.

In drug discovery, the 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one molecule serves as a platform for the development of novel therapeutics. Its structural flexibility allows for the incorporation of various functional groups, enabling the design of compounds with enhanced potency and selectivity. This adaptability is a significant advantage in the quest for targeted therapies that minimize side effects and improve patient outcomes.

Recent computational studies have provided insights into the molecular interactions of 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one with biological targets. Molecular docking simulations have identified potential binding sites on key enzymes and receptors, which could guide the development of more effective analogs. These computational tools are increasingly being integrated into drug discovery pipelines to accelerate the identification of promising candidates.

Despite its promising applications, the 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one compound faces challenges in clinical translation. Issues such as toxicity, pharmacokinetic limitations, and the need for further preclinical testing must be addressed before it can be considered for therapeutic use. Collaborative efforts between academia and industry are essential to overcome these barriers and bring this compound to the forefront of pharmaceutical innovation.

Overall, 6-(4-bromophenyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one represents a significant advancement in the field of medicinal chemistry. Its unique structural features and diverse biological activities position it as a valuable asset in the development of novel therapeutics. Continued research and collaboration will be crucial in unlocking its full potential and addressing the challenges associated with its clinical application.

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