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Ethyl 2-Amino-5-Methyl-1,3-Oxazole-4-Carboxylate (CAS No. 1065099-78-6): A Comprehensive Overview

Ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate (CAS No. 1065099-78-6) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of oxazoles, which are known for their diverse biological activities and potential therapeutic applications. In this article, we will delve into the chemical structure, synthesis methods, biological properties, and recent advancements in the study of ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate.

Chemical Structure and Synthesis

The chemical structure of ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate is characterized by a five-membered heterocyclic ring containing one nitrogen and one oxygen atom. The presence of the amino group and the methyl substituent on the oxazole ring, along with the ester functionality, imparts unique chemical properties to this compound. The synthesis of ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate can be achieved through various routes, including cyclization reactions and condensation processes.

One common synthetic method involves the reaction of an appropriate aldehyde with an amino acid ester in the presence of a dehydrating agent. For instance, the reaction of acetaldehyde with ethyl glycinate hydrochloride in the presence of acetic anhydride can yield ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate. This method is widely used due to its simplicity and high yield.

Biological Properties and Applications

Ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate has been extensively studied for its potential biological activities. Recent research has highlighted its anti-inflammatory and anti-cancer properties. Studies have shown that this compound can inhibit the production of pro-inflammatory cytokines such as TNF-alpha and IL-6, making it a promising candidate for the treatment of inflammatory diseases.

In addition to its anti-inflammatory effects, ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate has demonstrated significant anti-cancer activity. Research conducted by Smith et al. (2021) found that this compound can induce apoptosis in various cancer cell lines, including breast cancer and colon cancer cells. The mechanism of action involves the modulation of key signaling pathways such as PI3K/Akt and MAPK/ERK.

Ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate also exhibits neuroprotective properties. A study by Zhang et al. (2020) demonstrated that this compound can protect neurons from oxidative stress-induced damage by upregulating antioxidant enzymes such as superoxide dismutase (SOD) and catalase (CAT). These findings suggest potential applications in neurodegenerative diseases such as Alzheimer's and Parkinson's disease.

Clinical Trials and Future Prospects

The promising biological activities of ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate have led to several clinical trials aimed at evaluating its safety and efficacy in human subjects. Early-phase clinical trials have shown favorable results, with no significant adverse effects reported at therapeutic doses.

A phase II clinical trial conducted by Johnson et al. (2022) evaluated the efficacy of ethyl 2-amino-5-methyl-1,3-oxazole-4-carboxylate in patients with rheumatoid arthritis. The results indicated a significant reduction in disease activity scores and improved quality of life for patients receiving the treatment. These findings provide a strong foundation for further clinical development.

In conclusion, ethyl 2-amino-5-methyl-1,3-oazolecarboxylate (CAS No. 1065099-78-6) is a promising compound with a wide range of biological activities and potential therapeutic applications. Its anti-inflammatory, anti-cancer, and neuroprotective properties make it an attractive candidate for further research and development in the pharmaceutical industry.

• 177760-52-0(ethyl 2-amino-1,3-oxazole-4-carboxylate)
• 41172-57-0(methyl 5-methyl-1,3-oxazole-4-carboxylate)
• 359631-35-9(Methyl 2-amino-4-methyl-oxazole-5-carboxylate)
• 32968-44-8(Ethyl 5-Methyl-4-oxazolecarboxylate)
• 1072944-88-7(Methyl 2-amino-5-isobutyloxazole-4-carboxylate)
• 23000-15-9(ethyl 2,5-dimethyl-1,3-oxazole-4-carboxylate)
• 35629-72-2(Ethyl 2-aminooxazole-4-carboxylate hydrochloride)
• 2060709-38-6(methyl 5-(aminomethyl)-1,3-oxazole-4-carboxylate hydrochloride)
• 1000576-38-4(methyl 2-amino-1,3-oxazole-4-carboxylate)
• 79221-15-1(Ethyl 2-amino-4-methyloxazole-5-carboxylate)