351410-62-3 | 5-FLUORO-2-METHOXYNICOTINALDEHYDE

CAS:351410-62-3 | 5-FLUORO-2-METHOXYNICOTINALDEHYDE,Description

5-Fluoro-2-methoxynicotinaldehyde is a compound that is structurally related to various fluorinated heterocyclic compounds that have been studied for their potential biological activities. Although the specific compound is not directly mentioned in the provided papers, the research on similar fluorinated compounds provides insights into the chemical behavior and potential applications of such molecules. For instance, fluorinated naphthyridone derivatives have been synthesized and evaluated for their antibacterial properties, indicating the relevance of fluorinated compounds in medicinal chemistry.

Synthesis Analysis

The synthesis of fluorinated compounds often involves the introduction of a fluorine atom or a fluorinated group into a heterocyclic framework. In the case of the 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone derivatives, the synthesis likely involves multiple steps, including the formation of the naphthyridone core followed by the introduction of the fluorine atom and the methoxy or hydroxy groups. The specific methods and conditions used for the synthesis can greatly affect the yield and purity of the final product.

Molecular Structure Analysis

The molecular structure of fluorinated compounds can significantly influence their chemical reactivity and biological activity. For example, the presence of a fluorine atom can affect the electronic distribution within the molecule, potentially enhancing its ability to interact with biological targets. The tautomerism observed in 5-fluoro-4-hydroxy-2-methoxypyrimidine, which is structurally similar to 5-fluoro-2-methoxynicotinaldehyde, suggests that such compounds can exist in different forms depending on the environmental conditions, such as solvent and pH.

Chemical Reactions Analysis

Fluorinated aldehydes can participate in various chemical reactions, including aldol reactions, which are important for constructing carbon-carbon bonds. The study of a fluorogenic aldehyde with a 1,2,3-triazole moiety demonstrates the utility of such compounds in monitoring reaction progress through changes in fluorescence. This indicates that 5-fluoro-2-methoxynicotinaldehyde could potentially be used in similar applications, where its reactivity could be exploited in synthetic chemistry or bioconjugation reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluorinated compounds are often distinct from their non-fluorinated counterparts. For instance, the introduction of a methoxy group in the 5-position of a fluorinated naphthyridone derivative was found to be tolerated, suggesting that such modifications can be used to fine-tune the properties of the molecule without significantly diminishing its biochemical potency. Additionally, the solvation effects observed in tautomeric fluorinated pyrimidines highlight the importance of solvent interactions in determining the stability and behavior of such compounds.

Scientific Research Applications

Application 1: Inhibition of Cancer Cell Proliferation

• Summary of the Application : 5-Fluoro-2-methoxynicotinaldehyde is used as a DNA methylation inhibitor to prevent the proliferation of cancer cells. It is currently in phase II clinical trial.
• Methods of Application : The compound is administered to various cell lines established from different sarcomas. The toxicity of 5-Fluoro-2-methoxynicotinaldehyde is then analyzed.
• Results or Outcomes : The compound was found to inhibit HCT116, a colon cancer cell line, at the G2/M checkpoint and up-regulated the expression of multiple cancer-related genes. This could be due to its inhibitory activity towards DNA methylation.

Application 2: α-Glucosidase Inhibitor

• Summary of the Application : 5-Fluoro-2-methoxynicotinaldehyde is used to develop novel α-glucosidase inhibitors. These inhibitors prevent the digestion of carbohydrates and reduce the impact of carbohydrates on blood glucose.
• Methods of Application : A series of 5-fluoro-2-oxindole derivatives were synthesized and their α-glucosidase inhibitory activities were investigated.
• Results or Outcomes : The results of this investigation are not provided in the source.

Safety And Hazards

5-Fluoro-2-methoxynicotinaldehyde is classified as having acute toxicity (Category 4) for oral, dermal, and inhalation exposure. It may cause skin irritation (Category 2), serious eye irritation (Category 2), and respiratory irritation. It is also identified as having specific target organ toxicity with single exposure (Category 3).

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