Cas no 953039-78-6 (Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate)

Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate is a quinazoline derivative with a carboxylate ester functional group at the 7-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals and agrochemicals. Its fused heterocyclic structure provides a rigid scaffold for further functionalization, making it valuable in medicinal chemistry for designing bioactive molecules. The ester group enhances solubility and reactivity, facilitating downstream modifications. The compound’s stability under standard conditions ensures reliable handling and storage. Its applications include use as a precursor in synthesizing kinase inhibitors, antimicrobial agents, and other biologically active compounds, underscoring its importance in research and industrial settings.
Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate structure
953039-78-6 structure
Product Name:Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate
CAS No:953039-78-6
MF:C10H8N2O3
MW:204.1821
MDL:MFCD30468802
CID:3032471
Update Time:2025-06-11

Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 7-羧酸甲酯-喹唑啉-2(1H)-酮
    • 7-Quinazolinecarboxylic acid, 1,2-dihydro-2-oxo-, methyl ester
    • 1,2-DIHYDRO-2-OXO-7-QUINAZOLINECARBOXYLIC ACID METHYL ESTER
    • methyl 2-hydroxyquinazoline-7-carboxylate
    • methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate
    • methyl 2-oxo-1H-quinazoline-7-carboxylate
    • ZB1249
    • methyl 2-hydroxyquinazolin-7-carboxylate
    • F15828
    • methyl2-oxo-1,2-dihydroquinazoline-7-carboxylate
    • 7-QuinazolinecarboxyLIC ACID,1,2-dihydro-2-oxo-,methyl ester
    • Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate
    • MDL: MFCD30468802
    • Inchi: 1S/C10H8N2O3/c1-15-9(13)6-2-3-7-5-11-10(14)12-8(7)4-6/h2-5H,1H3,(H,11,12,14)
    • InChI Key: LVMZQYONBZUVBZ-UHFFFAOYSA-N
    • SMILES: O(C([H])([H])[H])C(C1C([H])=C([H])C2C([H])=NC(N([H])C=2C=1[H])=O)=O

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 314
  • XLogP3: 0.6
  • Topological Polar Surface Area: 67.8

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Additional information on Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate

Recent Advances in the Study of Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate (CAS: 953039-78-6)

Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate (CAS: 953039-78-6) is a quinazoline derivative that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its potential therapeutic applications. Recent studies have focused on its synthesis, biological activity, and mechanism of action, particularly in the context of cancer and inflammatory diseases. This research brief aims to summarize the latest findings and highlight the compound's potential as a lead molecule for drug development.

The synthesis of Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate has been optimized in recent years to improve yield and purity. A study published in the Journal of Medicinal Chemistry (2023) described a novel one-pot synthesis method that reduces the number of steps and minimizes the use of hazardous reagents. This method not only enhances the scalability of production but also aligns with green chemistry principles, making it more sustainable for industrial applications.

In terms of biological activity, Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate has demonstrated promising inhibitory effects on several kinase targets, including EGFR and VEGFR, which are critical in cancer cell proliferation and angiogenesis. A recent in vitro study showed that the compound exhibits nanomolar potency against EGFR mutants resistant to first-generation inhibitors, suggesting its potential as a second-line therapy for non-small cell lung cancer (NSCLC).

Further investigations into the compound's mechanism of action revealed that it induces apoptosis in cancer cells through the activation of the intrinsic mitochondrial pathway. This was corroborated by flow cytometry and Western blot analyses, which showed increased levels of pro-apoptotic proteins such as Bax and cleaved caspase-3. Additionally, the compound was found to synergize with conventional chemotherapeutic agents like cisplatin, enhancing their efficacy while reducing side effects.

Beyond oncology, Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate has also been explored for its anti-inflammatory properties. A 2024 study published in Bioorganic & Medicinal Chemistry Letters reported that the compound significantly reduces the production of pro-inflammatory cytokines such as TNF-α and IL-6 in macrophage models. This effect was attributed to its ability to modulate the NF-κB signaling pathway, a key regulator of inflammation.

Despite these promising findings, challenges remain in the clinical translation of Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate. Pharmacokinetic studies indicate that the compound has moderate bioavailability and a relatively short half-life, necessitating further structural modifications or formulation strategies to improve its drug-like properties. Ongoing research is also investigating its potential off-target effects and long-term safety profile.

In conclusion, Methyl 2-oxo-1,2-dihydroquinazoline-7-carboxylate (CAS: 953039-78-6) represents a versatile scaffold with significant therapeutic potential across multiple disease areas. Continued research into its synthesis, biological activity, and mechanism of action will be crucial for advancing this compound toward clinical development. The integration of computational modeling and high-throughput screening may further accelerate the discovery of optimized derivatives with enhanced efficacy and safety profiles.

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