2454397-74-9 | 3-Pyridinecarboxylic acid, 4-amino-6-chloro-5-fluoro-, ethyl ester

CAS:2454397-74-9 | 3-Pyridinecarboxylic acid, 4-amino-6-chloro-5-fluoro-, ethyl ester,Description

Ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate is a derivative of pyridine. It is a type of carboxylate ester and can be used as a pharmaceutical intermediate.

Molecular Structure Analysis

The molecular structure of ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate is characterized by the presence of a pyridine ring which is a six-membered ring with one nitrogen atom. The pyridine ring is substituted at the 4th position by an amino group, at the 6th position by a chloro group, and at the 5th position by a fluoro group. The 3rd position of the pyridine ring is substituted by a carboxylate group, which is further esterified with an ethyl group.

Physical And Chemical Properties Analysis

The boiling point of ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate is predicted to be 322.3±42.0 °C and its density is predicted to be 1.405±0.06 g/cm3. The pKa, a measure of the acidity of the compound, is predicted to be 0.73±0.50.

Scientific Research Applications

Synthesis of Antibacterial Agents

Ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate has been explored in the synthesis of pyridonecarboxylic acids, serving as a precursor for various antibacterial agents. For instance, a study detailed the synthesis and antibacterial activity of pyridonecarboxylic acid derivatives, indicating that certain compounds exhibited significant antibacterial efficacy, surpassing that of known agents like enoxacin, and warranted further biological evaluation (Egawa et al., 1984). This underscores the role of ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate in the development of new antibacterial compounds, highlighting its potential in addressing the growing concern of antibiotic resistance.

Cancer Research

In cancer research, derivatives of ethyl 4-amino-6-chloro-5-fluoropyridine-3-carboxylate have been synthesized and evaluated for their potential anticancer properties. A particular study focused on the synthesis of pyrido[4,3-b][1,4]oxazines and pyrido[4,3-b][1,4]thiazines, examining their effects on the proliferation and mitotic index of cultured L1210 cells and their impact on the survival of mice bearing P388 leukemia. The findings revealed that some of these compounds exhibited promising anticancer activity, suggesting the chemical's utility in developing novel therapeutic agents (Temple et al., 1983).

Chemical Synthesis and Modification

The compound has also been utilized in chemical synthesis and modification processes. For instance, its analogues were involved in reactions leading to the creation of fluorinated pyridines, which serve as critical intermediates in the synthesis of various pharmaceutical agents, including those with antibacterial properties. This illustrates the compound's versatility in organic synthesis, enabling the development of fluorinated compounds with enhanced biological activities (Matsumoto et al., 1984).

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