Cas no 1206975-02-1 (Methyl 1-chloroisoquinoline-7-carboxylate)

Methyl 1-chloroisoquinoline-7-carboxylate is a versatile heterocyclic building block used in organic synthesis and pharmaceutical research. Its structure features a reactive chlorinated isoquinoline core coupled with an ester functional group, enabling further derivatization through nucleophilic substitution or hydrolysis. The compound is particularly valuable in medicinal chemistry for constructing biologically active scaffolds, including potential kinase inhibitors and antimicrobial agents. Its crystalline form ensures consistent purity, while the methyl ester group enhances solubility in common organic solvents, facilitating downstream reactions. The product is typically handled under inert conditions to preserve stability. Suitable for cross-coupling, amidation, and other transformations, it serves as a key intermediate in complex molecule synthesis.
Methyl 1-chloroisoquinoline-7-carboxylate structure
1206975-02-1 structure
Product Name:Methyl 1-chloroisoquinoline-7-carboxylate
CAS No:1206975-02-1
MF:C11H8ClNO2
MW:221.639721870422
MDL:MFCD18250895
CID:1213843
PubChem ID:72213627
Update Time:2025-05-22

Methyl 1-chloroisoquinoline-7-carboxylate Chemical and Physical Properties

Names and Identifiers

    • methyl 1-chloroisoquinoline-7-carboxylate
    • METHYL1-CHLOROISOQUINOLINE-7-CARBOXYLATE
    • 1206975-02-1
    • AB73874
    • PS-11217
    • CS-0454093
    • MFCD18250895
    • 1-Chloro-7-(methoxycarbonyl)isoquinoline, 1-Chloro-7-(methoxycarbonyl)-2-azanaphthalene
    • AKOS022879585
    • D79788
    • Methyl 1-chloroisoquinoline-7-carboxylate
    • MDL: MFCD18250895
    • Inchi: 1S/C11H8ClNO2/c1-15-11(14)8-3-2-7-4-5-13-10(12)9(7)6-8/h2-6H,1H3
    • InChI Key: SZKDMOYPYAUGPM-UHFFFAOYSA-N
    • SMILES: ClC1C2C=C(C(=O)OC)C=CC=2C=CN=1

Computed Properties

  • Exact Mass: 221.0243562g/mol
  • Monoisotopic Mass: 221.0243562g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 247
  • 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: 2.9
  • Topological Polar Surface Area: 39.2?2

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Additional information on Methyl 1-chloroisoquinoline-7-carboxylate

Recent Advances in the Application of Methyl 1-chloroisoquinoline-7-carboxylate (CAS: 1206975-02-1) in Chemical Biology and Pharmaceutical Research

Methyl 1-chloroisoquinoline-7-carboxylate (CAS: 1206975-02-1) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its unique isoquinoline scaffold and functional groups, serves as a critical building block in the synthesis of various bioactive molecules. Recent studies have highlighted its potential in drug discovery, particularly in the development of kinase inhibitors and anti-inflammatory agents. The compound's ability to undergo diverse chemical transformations makes it a valuable intermediate for the construction of complex molecular architectures.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers explored the use of Methyl 1-chloroisoquinoline-7-carboxylate as a precursor for the synthesis of novel kinase inhibitors. The study demonstrated that derivatives of this compound exhibited potent inhibitory activity against several tyrosine kinases, including EGFR and VEGFR, which are implicated in cancer progression. The researchers employed a combination of computational modeling and synthetic chemistry to optimize the compound's structure, resulting in derivatives with improved selectivity and pharmacokinetic properties. These findings underscore the compound's potential as a scaffold for targeted cancer therapies.

Another notable application of Methyl 1-chloroisoquinoline-7-carboxylate was reported in a 2022 article in Bioorganic & Medicinal Chemistry Letters. The study focused on the compound's role in the development of anti-inflammatory agents. By modifying the isoquinoline core, researchers synthesized a series of derivatives that exhibited significant inhibition of pro-inflammatory cytokines such as TNF-α and IL-6. The lead compound from this series showed promising results in preclinical models of rheumatoid arthritis, suggesting its potential for further development as a therapeutic agent. The study also highlighted the compound's favorable safety profile, which is a critical consideration in drug development.

Beyond its applications in drug discovery, Methyl 1-chloroisoquinoline-7-carboxylate has also been investigated for its utility in chemical biology. A 2023 study in ACS Chemical Biology described the use of this compound as a fluorescent probe for studying protein-ligand interactions. The researchers functionalized the isoquinoline core with a fluorophore, enabling real-time monitoring of binding events in live cells. This approach provides a powerful tool for elucidating the mechanisms of action of potential drug candidates and could accelerate the discovery of new therapeutics.

In conclusion, Methyl 1-chloroisoquinoline-7-carboxylate (CAS: 1206975-02-1) represents a versatile and valuable compound in chemical biology and pharmaceutical research. Its applications span from drug discovery to chemical probes, highlighting its broad utility. Future research directions may include further optimization of its derivatives for enhanced bioactivity and the exploration of its potential in other therapeutic areas. As the field continues to evolve, this compound is likely to remain a focal point of innovation and discovery.

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