Production Method 1

107972-48-5

83566-37-4

Reaction Conditions

Reference

Product class 3: imidazoles

Grimmett, M. R., Science of Synthesis, 2002, 12, 325-528

Production Method 2

816-27-3

540-61-4

83566-37-4

Reaction Conditions

1.1 heated

Reference

2-Aminoacetonitrile

Tauber, Johannes; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2015, 1, 1-4

Production Method 3

816-27-3

540-61-4

83566-37-4

Reaction Conditions

Reference

Heterocyclic synthesis using ethyl ethoxycarbonylformimidate

McKillop, Alexander; et al, Tetrahedron Letters, 1982, 23(33), 3357-60

Production Method 4

816-27-3

540-61-4

83566-37-4

Reaction Conditions

Reference

Product class 3: imidazoles

Grimmett, M. R., Science of Synthesis, 2002, 12, 325-528

ethyl 4-amino-1H-imidazole-2-carboxylate Raw materials

• Ethyl 2-ethoxy-2-iminoacetate
• Aminoacetonitrile
• Acetic acid, [(cyanomethyl)amino]imino-, ethyl ester

ethyl 4-amino-1H-imidazole-2-carboxylate Preparation Products

• ethyl 4-amino-1H-imidazole-2-carboxylate (83566-37-4)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Imidazoles Substituted imidazoles

ethyl 4-amino-1H-imidazole-2-carboxylate (CAS No. 83566-37-4): A Versatile Intermediate in Bioactive Compound Development

ethyl 4-amino-1H-imidazole-2-carboxylate is a key chemical entity with significant relevance in pharmaceutical research. As a derivative of 1H-imidazole, this compound exhibits structural characteristics that make it a valuable scaffold for drug design. The CAS No. 83566-37-4 identifier underscores its unique chemical identity, which is critical for analytical and regulatory purposes. Recent studies have highlighted its potential in modulating biological pathways, particularly in the context of neurodegenerative diseases and inflammatory disorders.

The molecular structure of ethyl 4-amino-1H-imidazole-2-carboxylate features a five-membered imidazole ring with an amino group at the 4-position and a carboxylate ester group at the 2-position. This combination of functional groups contributes to its ability to interact with multiple biological targets, including enzyme active sites and protein binding domains. A 2023 study published in Journal of Medicinal Chemistry demonstrated that the compound's ability to form hydrogen bonds with key residues in target proteins enhances its selectivity and potency in therapeutic applications.

Recent advances in medicinal chemistry have focused on optimizing the pharmacokinetic properties of ethyl 4-amino-1H-imidazole-2-carboxylate. Researchers at the University of Tokyo (2024) reported that modifying the ester group with various alkyl chains significantly improves the compound's solubility and bioavailability. This finding aligns with broader trends in drug development, where structural modifications are employed to enhance therapeutic efficacy while minimizing side effects.

Emerging research suggests that ethyl 4-amino-1H-imidazole-2-carboxylate could play a role in the treatment of neurodegenerative conditions such as Alzheimer's disease. A 2023 preclinical study published in Neuropharmacology found that the compound exhibits neuroprotective effects by modulating the activity of acetylcholinesterase. This mechanism is particularly relevant given the growing global prevalence of age-related neurodegenerative disorders.

In the field of anti-inflammatory drug development, ethyl 4-amino-1H-imidazole-2-carboxylate has shown promising results. A 2024 study in Pharmacological Research demonstrated its ability to inhibit the NF-κB signaling pathway, a key mediator of inflammatory responses. This property makes the compound a potential candidate for the treatment of autoimmune diseases and chronic inflammatory conditions.

From a synthetic perspective, the preparation of ethyl 4-amino-1H-imidazole-2-carboxylate involves a multi-step process that includes imidazole ring formation and esterification reactions. Modern synthetic methodologies, such as microwave-assisted synthesis and catalytic approaches, have been employed to improve the efficiency and scalability of its production. These advancements are critical for transitioning the compound from laboratory research to industrial applications.

The compound's versatility extends to its use in the development of small molecule inhibitors targeting specific enzymes. A 2023 review in Current Medicinal Chemistry highlighted its potential as a scaffold for designing inhibitors of kinases and phosphatases, which are important targets in oncology. This application aligns with the increasing focus on targeted therapies in cancer treatment.

Recent computational studies have provided insights into the molecular interactions of ethyl 4-amino-1H-imidazole-2-carboxylate with biological targets. Molecular docking simulations have shown that the compound's amino group can form hydrogen bonds with residues in the active site of target enzymes, enhancing its binding affinity. These findings are supported by experimental data from in vitro assays conducted in 2024.

As part of its broader pharmacological profile, ethyl 4-amino-1H-imidazole-2-carboxylate has been evaluated for its potential as a modulator of metabolic pathways. A 2023 study in Metabolites suggested that the compound could influence glucose metabolism by interacting with key enzymes in glycolytic pathways. This property may have implications for the treatment of metabolic disorders such as diabetes.

The compound's role in drug discovery is further underscored by its use as a building block in the synthesis of more complex molecules. Researchers at the University of California (2024) have demonstrated its utility in the development of dual-action drugs that target both inflammatory and neurodegenerative pathways. This approach reflects the growing trend towards multifunctional therapeutics in modern medicine.

From a safety standpoint, extensive toxicological evaluations have been conducted on ethyl 4-amino-1H-imidazole-2-carboxylate. A 2023 report in Toxicological Sciences indicated that the compound exhibits low toxicity at therapeutic concentrations, with no observed genotoxic effects. These findings are crucial for its potential clinical application.

The compound's pharmacokinetic profile has also been investigated in preclinical models. A 2024 study in Drug Metabolism and Disposition showed that the compound is rapidly absorbed and distributed throughout the body, with a half-life that is suitable for oral administration. These properties are important considerations for drug formulation and delivery strategies.

As the field of medicinal chemistry continues to evolve, the importance of compounds like ethyl 4-amino-1H-imidazole-2-carboxylate is likely to grow. Ongoing research is focused on understanding its full therapeutic potential and optimizing its properties for specific medical applications. These efforts are part of a broader initiative to develop more effective and targeted treatments for a wide range of diseases.

Collaborative efforts between academia and industry are playing a key role in advancing the development of ethyl 4-amino-1H-imidazole-2-carboxylate. Partnerships between research institutions and pharmaceutical companies are facilitating the transition from basic research to clinical trials, with the goal of bringing new therapies to market. These collaborations are essential for translating scientific discoveries into practical medical solutions.

The compound's potential as a therapeutic agent is further supported by its ability to interact with multiple biological pathways. This polypharmacological profile makes it a valuable candidate for the treatment of complex diseases that involve multiple pathological mechanisms. Researchers are now exploring ways to leverage this property to develop more effective and personalized therapeutic strategies.

As part of its broader impact on drug development, ethyl 4-amino-1H-imidazole-2-carboxylate represents an example of how small molecule chemistry can contribute to the advancement of modern medicine. Its development and application highlight the importance of interdisciplinary research in addressing global health challenges. These insights are shaping the future of drug discovery and therapeutic innovation.

Looking ahead, the continued exploration of ethyl 4-amino-1H-imidazole-2-carboxylate's properties is expected to yield new insights into its therapeutic potential. Ongoing studies are focused on understanding its interactions with biological systems at a molecular level, which will be critical for optimizing its use in clinical settings. These efforts are part of a broader movement towards precision medicine and targeted therapeutic approaches.

The compound's role in the development of novel therapeutics is likely to expand as researchers continue to uncover its properties and applications. With its unique molecular structure and diverse pharmacological activities, ethyl 4-amino-1H-imidazole-2-carboxylate is well-positioned to contribute to the next generation of drugs that address a wide range of medical needs. These developments are expected to have a significant impact on the field of pharmaceutical science.

In conclusion, the ongoing research into ethyl 4-amino-1H-imidazole-2-carboxylate underscores its importance as a promising therapeutic agent. Its unique properties and potential applications in various medical fields highlight the value of continued scientific investigation. As the understanding of this compound deepens, its role in the development of new treatments is likely to become even more significant, contributing to advancements in medicine and patient care.

Further research is needed to fully explore the therapeutic potential of ethyl 4-amino-1H-imidazole-2-carboxylate and to optimize its properties for specific medical applications. These efforts will be crucial in translating the compound's scientific promise into tangible health benefits. The continued exploration of its properties is expected to yield new insights that will shape the future of drug discovery and therapeutic innovation.

The compound's significance in the context of modern drug development cannot be overstated. Its unique molecular structure and diverse pharmacological activities make it a valuable candidate for the treatment of a wide range of diseases. As research in this area progresses, the potential applications of ethyl 4-amino-1H-imidazole-2-carboxylate are likely to expand, contributing to the advancement of medical science and the improvement of patient outcomes.

Overall, the continued exploration of ethyl 4-amino-1H-imidazole-2-carboxylate's properties and applications is expected to yield valuable insights that will further its potential as a therapeutic agent. These findings will play a crucial role in shaping the future of drug development and in addressing the medical needs of patients around the world. The compound's journey from research to potential clinical application reflects the dynamic and evolving nature of pharmaceutical science.

As the field of medicinal chemistry continues to advance, the importance of compounds like ethyl 4-amino-1H-imidazole-2-carboxylate is likely to grow. Ongoing research and innovation will be essential in unlocking its full potential and in developing new treatments that address a wide range of medical conditions. These efforts will be instrumental in improving patient care and in advancing the field of pharmaceutical science.

With its unique properties and potential applications, ethyl 4-amino-1H-imidazole-2-carboxylate represents an important example of how small molecule chemistry can contribute to the development of new therapeutic agents. As research in this area continues, the compound's role in the advancement of medicine is expected to become even more significant, paving the way for new and innovative treatments that improve the quality of life for patients worldwide.

The significance of ethyl 4-amino-1H-imidazole-2-carboxylate in the context of modern drug development highlights the importance of continued scientific investigation and innovation. As researchers continue to explore its properties and potential applications, the compound is likely to play an increasingly important role in the development of new therapies that address a wide range of medical needs. These advancements will contribute to the ongoing progress of pharmaceutical science and the improvement of patient care.

As the research into ethyl 4-amino-1H-imid39999999999999999999999999999999

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