Ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
[CAS# 144060-96-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: Ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate
• Molecular Formula: C₁₇H₂₀BrNO₃S
• Molecular Weight: 398.31
• CAS Registry Number: 144060-96-8
• SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC(=C(C=C2)OCC(C)C)Br)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P351

Discovery and Applications

Ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is a chemical compound with a distinctive structure and potential utility in various fields of chemistry and medicine. With the formula C18H20BrNO3S, this compound features a thiazole ring substituted with an ethyl ester, a brominated phenyl group, and an isobutoxy group. Its unique combination of functional groups provides interesting properties that have been explored for different applications.

The compound was first synthesized in the context of developing new chemical entities with potential biological activities. The introduction of the bromine atom and the isobutoxy group into the phenyl ring is designed to enhance the reactivity and biological profile of the compound. The thiazole ring is known for its versatility and biological significance, making it an ideal scaffold for exploring various pharmacological effects.

The synthesis of ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate involves several steps. The process typically starts with the preparation of the thiazole ring, followed by the introduction of the ethyl ester and the phenyl substituents. The bromination of the phenyl ring and the installation of the isobutoxy group are crucial steps in the synthesis. The compound is usually purified through chromatography and characterized using techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry.

One of the notable applications of ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is in medicinal chemistry, where it is investigated for its potential therapeutic properties. The thiazole ring is a key feature in many biologically active compounds, and derivatives like this one are explored for their effects on various biological targets. Research has shown that thiazole derivatives can exhibit a range of pharmacological activities, including antimicrobial, anti-inflammatory, and anticancer effects. Ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is evaluated for its potential to act as an effective drug candidate in these areas.

In particular, the compound's structure suggests potential utility in developing new antimicrobial agents. The brominated phenyl group and the thiazole ring may enhance the compound's ability to interact with microbial targets and inhibit their growth. Studies may focus on its effectiveness against bacterial or fungal infections and its potential as a lead compound for further drug development.

Additionally, the compound's structure is of interest for its possible use in designing new anticancer agents. Thiazole derivatives are known to affect cellular processes related to cancer, such as cell proliferation and apoptosis. Ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate could be explored for its ability to modulate these processes and provide therapeutic benefits in cancer treatment.

Furthermore, the synthesis and characterization of ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate contribute to the broader field of organic synthesis and chemical research. The compound serves as an example of how modifying traditional scaffolds with different functional groups can lead to new and valuable chemical entities.

Overall, ethyl 2-(3-bromo-4-isobutoxyphenyl)-4-methyl-5-thiazolecarboxylate is a compound with promising applications in medicinal chemistry and drug development. Its unique structure offers opportunities for exploring its biological activities and developing new therapeutic agents.

References

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