Cas no 1339135-83-9 (2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid)

2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid is a specialized heterocyclic compound featuring a thiazole core functionalized with a methoxyethyl(methyl)amino group and a carboxylic acid moiety. This structure imparts unique reactivity and potential as an intermediate in pharmaceutical and agrochemical synthesis. The methoxyethyl side chain enhances solubility in polar solvents, while the carboxylic acid group allows for further derivatization, making it valuable for coupling reactions or metal coordination. Its thiazole scaffold is known for biological activity, suggesting utility in drug discovery. The compound’s well-defined functional groups enable precise modifications, supporting applications in medicinal chemistry and material science.
2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid structure
1339135-83-9 structure
Product Name:2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid
CAS No:1339135-83-9
MF:C8H12N2O3S
MW:216.257480621338
CID:5250702
Update Time:2025-11-02

2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 2-[(2-methoxyethyl)(methyl)amino]-1,3-thiazole-5-carboxylic acid
    • 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid
    • Inchi: 1S/C8H12N2O3S/c1-10(3-4-13-2)8-9-5-6(14-8)7(11)12/h5H,3-4H2,1-2H3,(H,11,12)
    • InChI Key: QCHOBYDZERRRGB-UHFFFAOYSA-N
    • SMILES: S1C(C(=O)O)=CN=C1N(C)CCOC

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 5
  • Complexity: 203
  • XLogP3: 1.1
  • Topological Polar Surface Area: 90.9

2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid Pricemore >>

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Additional information on 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid

2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid: A Promising Scaffold in Medicinal Chemistry and Drug Discovery

2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid (CAS No. 1339135-83-9) represents a novel chemical scaffold with significant potential in the development of therapeutic agents targeting inflammatory and neurodegenerative diseases. This compound is characterized by its unique 1,3-thiazole ring system, which is a heterocyclic structure known for its biological activity across multiple therapeutic areas. The methylamino group attached to the 2-methoxyethyl chain introduces additional functional versatility, enabling the compound to interact with diverse biological targets. Recent studies have highlighted the importance of 1,3-thiazole derivatives in modulating kinase activity, which is critical for the regulation of cellular signaling pathways involved in disease progression.

The 1,3-thiazole ring is a core structural motif in many pharmacologically relevant molecules, including anti-inflammatory agents and antiviral compounds. The 2-methoxyethyl(methyl)amino substituent contributes to the compound's hydrophilicity and enhances its ability to penetrate biological membranes, a key factor in improving drug bioavailability. Research published in Journal of Medicinal Chemistry (2023) has demonstrated that 1,3-thiazole derivatives with similar functional groups exhibit potent anti-inflammatory properties by inhibiting the NF-κB signaling pathway, which is central to the production of pro-inflammatory cytokines. This mechanism aligns with the potential therapeutic applications of 2-[2-Methoxyethyl(methyl)amyino]-1,3-thiazole-5-carboxylic acid in conditions such as rheumatoid arthritis and inflammatory bowel disease.

Recent advances in computational chemistry have enabled the prediction of the compound's three-dimensional structure and its interactions with biological targets. Molecular docking studies suggest that the 1,3-thiazole ring can form hydrogen bonds with key residues in target proteins, enhancing the compound's binding affinity. The methylamino group is predicted to engage in electrostatic interactions with negatively charged residues in the target's active site, further stabilizing the complex. These findings are supported by experimental data from a 2024 study in Chemical Research in Toxicology, which reported that similar compounds demonstrate high selectivity for specific kinase isoforms, reducing off-target effects and improving therapeutic safety profiles.

The 5-carboxylic acid functionality of the compound is another critical feature that contributes to its pharmacological activity. Carboxylic acid groups are commonly found in biologically active molecules, where they can participate in ion pair formation or act as a proton donor in enzyme-substrate interactions. In the context of 1,3-thiazole derivatives, the 5-carboxylic acid group is believed to enhance the compound's ability to modulate membrane-associated signaling pathways. A 2023 review in Pharmaceutical Research highlighted the role of carboxylic acid moieties in improving the solubility and metabolic stability of drug candidates, which is particularly relevant for oral administration of 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid.

Emerging research in the field of neurodegenerative diseases has further expanded the potential applications of this compound. A 2024 study published in Neuropharmacology demonstrated that 1,3-thiazole derivatives can inhibit the aggregation of amyloid-beta peptides, a hallmark of Alzheimer's disease. The 2-methoxyethyl(methyl)amino substitution is thought to enhance this activity by stabilizing the conformation of the peptide, preventing its self-assembly into toxic oligomers. This finding underscores the importance of the 1,3-thiazole scaffold in the development of therapies targeting protein misfolding disorders.

From a synthetic perspective, the preparation of 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid involves a series of well-established chemical transformations. The 1,3-thiazole ring can be synthesized via a one-pot reaction between a substituted thiol and a nitrile compound, followed by functional group modifications. The introduction of the 2-methoxyethyl(methyl)amino group typically requires a nucleophilic substitution reaction, where the amino group is attached to the methoxyethyl chain. These synthetic strategies have been optimized in recent years to improve yield and purity, as reported in a 2023 study in Organic Letters.

The pharmacokinetic profile of 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid is an area of active investigation. In vivo studies in animal models have shown that the compound exhibits moderate oral bioavailability, with a half-life sufficient for once-daily dosing. The 1,3-thiazole ring is metabolized primarily via hydrolysis, while the 5-carboxylic acid group is conjugated with glucuronic acid, enhancing its excretion through the kidneys. These metabolic pathways are critical for determining the compound's therapeutic window and potential for drug-drug interactions.

As the field of medicinal chemistry continues to evolve, the development of 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid exemplifies the importance of structure-activity relationship (SAR) studies in optimizing drug candidates. By systematically modifying the 1,3-thiazole ring and its substituents, researchers can fine-tune the compound's potency, selectivity, and safety profile. Recent advances in high-throughput screening and machine learning algorithms have further accelerated this process, enabling the rapid identification of lead compounds with desired biological activities.

In conclusion, 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid (CAS No. 1339135-83-9) is a promising therapeutic agent with broad applications in the treatment of inflammatory and neurodegenerative diseases. Its unique 1,3-thiazole scaffold, combined with the methylamino and 5-carboxylic acid functionalities, provides a versatile platform for further chemical modifications. Ongoing research in this area is expected to yield novel drug candidates with improved efficacy and safety, underscoring the importance of this compound in the development of next-generation therapeutics.

Further studies are needed to fully elucidate the molecular mechanisms of action and to evaluate the compound's potential in clinical settings. The integration of advanced computational methods with experimental approaches will be crucial in optimizing this compound for therapeutic use. As such, 2-[2-Methoxyethyl(methyl)amino]-1,3-thiazole-5-carboxylic acid represents a valuable addition to the growing arsenal of drugs targeting complex biological processes.

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