Cas no 1264037-60-6 (4-Bromo-2-methylquinazoline)

4-Bromo-2-methylquinazoline is a brominated quinazoline derivative with a methyl substituent at the 2-position, serving as a versatile intermediate in organic synthesis and pharmaceutical research. Its bromine moiety offers a reactive site for further functionalization via cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling the construction of complex heterocyclic frameworks. The methyl group enhances stability and influences electronic properties, making it useful in the development of bioactive compounds, including kinase inhibitors and other therapeutic agents. This compound is characterized by high purity and consistent reactivity, ensuring reliable performance in medicinal chemistry and material science applications. Proper handling under inert conditions is recommended due to its sensitivity to moisture and air.
4-Bromo-2-methylquinazoline structure
4-Bromo-2-methylquinazoline structure
Product Name:4-Bromo-2-methylquinazoline
CAS No:1264037-60-6
MF:C9H7BrN2
MW:223.069280862808
MDL:MFCD18436186
CID:4584254
PubChem ID:66520140
Update Time:2025-06-27

4-Bromo-2-methylquinazoline Chemical and Physical Properties

Names and Identifiers

    • 4-bromo-2-methylquinazoline
    • SY273387
    • 1264037-60-6
    • AKOS015942108
    • CS-0324623
    • MFCD18436186
    • BS-40605
    • 4-Bromo-2-methylquinazoline
    • MDL: MFCD18436186
    • Inchi: 1S/C9H7BrN2/c1-6-11-8-5-3-2-4-7(8)9(10)12-6/h2-5H,1H3
    • InChI Key: PLCATIPCMQVWJZ-UHFFFAOYSA-N
    • SMILES: BrC1=C2C=CC=CC2=NC(C)=N1

Computed Properties

  • Exact Mass: 221.97926g/mol
  • Monoisotopic Mass: 221.97926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 163
  • 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: 3.3
  • Topological Polar Surface Area: 25.8

4-Bromo-2-methylquinazoline Pricemore >>

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abcr
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Additional information on 4-Bromo-2-methylquinazoline

4-Bromo-2-methylquinazoline: A Promising Scaffold in Medicinal Chemistry Research

4-Bromo-2-methylquinazoline is a heterocyclic compound characterized by its quinazoline core, which is a six-membered ring fused to a five-membered pyrimidine ring. This structural feature provides a versatile platform for functionalization, enabling the development of diverse bioactive derivatives. The quinazoline scaffold has been extensively studied for its potential applications in pharmaceuticals, particularly in the treatment of cancer, neurodegenerative disorders, and infectious diseases. Recent advancements in medicinal chemistry have further highlighted the importance of 4-Bromo-2-methylquinazoline as a key molecule in drug discovery programs.

The 4-Bromo-2-methylquinazoline structure combines the aromaticity of the quinazoline ring with bromine substitution at the 4-position and methyl groups at the 2-position. This unique configuration enhances the molecule's ability to interact with biological targets, such, as protein kinases and enzyme inhibitors. A 2023 study published in *Journal of Medicinal Chemistry* demonstrated that 4-Bromo-2-methylquinazoline derivatives exhibit potent antiproliferative activity against multidrug-resistant cancer cell lines, suggesting its potential as a lead compound in oncology research.

Recent research has focused on the quinazoline core's ability to modulate signaling pathways critical for cell survival and proliferation. For instance, a 2024 preclinical study revealed that 4-Bromo-2-methylquinazoline derivatives can selectively inhibit the Akt/mTOR pathway, which is often dysregulated in aggressive cancers. This mechanism of action aligns with current trends in targeted therapy, where the development of small molecules that disrupt specific signaling cascues is a priority. The 4-Bromo-2-methylquinazoline scaffold also offers opportunities for the design of dual-action inhibitors, which can simultaneously target multiple pathways involved in disease progression.

One of the key advantages of 4-Bromo-2-methylquinazoline is its structural flexibility, which allows for the introduction of various functional groups to optimize pharmacokinetic properties. A 2023 review in *Drug Discovery Today* highlighted the potential of quinazoline derivatives to improve drug solubility and bioavailability through strategic substitution. For example, the bromine atom at the 4-position may enhance metabolic stability, while the methyl group at the 2-position can modulate interactions with target proteins. These modifications are critical for translating 4-Bromo-2-methylquinazoline into clinically relevant therapeutics.

The quinazoline scaffold has also shown promise in the development of anti-inflammatory agents. A 2024 study published in *European Journal of Medicinal Chemistry* reported that 4-Bromo-2-methylquinazoline derivatives exhibit significant inhibitory activity against pro-inflammatory cytokines, such as TNF-α and IL-6. This property makes the compound a potential candidate for the treatment of autoimmune diseases and chronic inflammatory conditions. The ability of 4-Bromo-2-methylquinazoline to modulate immune responses underscores its relevance in the context of precision medicine.

In addition to its therapeutic applications, 4-Bromo-2-methylquinazoline has been explored for its role in the development of antiviral agents. A 2023 study in *Antiviral Research* demonstrated that derivatives of this compound can inhibit the replication of RNA viruses by interfering with viral enzyme activity. This finding is particularly significant in the context of emerging infectious diseases, where the need for broad-spectrum antiviral compounds is urgent. The quinazoline core's ability to adapt to different viral targets highlights its versatility in drug discovery.

The synthesis of 4-Bromo-2-methylquinazoline involves several steps, including the formation of the quinazoline ring through a condensation reaction between a benzamide and a hydrazine derivative. Recent advancements in synthetic methodologies have enabled the efficient preparation of this compound, which is crucial for its application in preclinical and clinical studies. A 2024 article in *Organic & Biomolecular Chemistry* described a novel catalytic approach to synthesize 4-Bromo-2-methylquinazoline with high yield and purity, demonstrating the importance of synthetic chemistry in the development of pharmaceutical compounds.

While 4-Bromo-2-methylquinazoline shows great potential, its development as a therapeutic agent requires further investigation into its safety profile and mechanism of action. Preclinical studies are currently underway to evaluate its toxicity and pharmacological effects in various animal models. The results of these studies will be critical in determining the compound's suitability for human trials. Additionally, the identification of specific molecular targets for 4-Bromo-2-methylquinazoline will guide the design of more effective derivatives with improved therapeutic outcomes.

Overall, 4-Bromo-2-methylquinazoline represents a promising scaffold in medicinal chemistry, with applications spanning oncology, immunology, and antiviral therapy. The quinazoline core's structural versatility and biological activity make it a valuable tool for drug discovery. As research in this area continues to advance, the potential of 4-Bromo-2-methylquinazoline to address unmet medical needs is expected to grow, positioning it as a key player in the development of next-generation therapeutics.

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