79660-46-1 | Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

CAS:79660-46-1 | Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate,Description

Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate is a compound that belongs to the quinolone family, a class of synthetic broad-spectrum antibacterial agents. Quinolones are known for their potent activity against a wide range of bacterial pathogens, including both Gram-positive and Gram-negative bacteria. The trifluoromethyl group at positions 6, 7, and 8 on the quinolone ring system is not commonly found in commercial quinolones, which typically have fluorine atoms at the 6 and/or 7 positions. This unique substitution pattern could potentially confer distinct physical, chemical, and biological properties to the compound.

Synthesis Analysis

The synthesis of related quinolone derivatives often involves multi-step reactions, starting from various substituted benzoic acids or their esters. For instance, the synthesis of ethyl 1-ethyl-6-fluoro-7-(fatty amido)-1,4-dihydro-4-oxoquinoline-3-carboxylate derivatives includes a key step of obtaining the C-7 fatty amide derivative through the selective formation of an azide followed by reduction to the corresponding amine. Another example is the preparation of 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-ethyl carboxylate, which involves acyl-chlorination, condensation, decarboxylation, esterification, cyclopropylamine replacement, and cyclization. These methods highlight the complexity and versatility of quinolone synthesis.

Molecular Structure Analysis

The molecular structure of quinolones is characterized by a bicyclic core consisting of a benzene ring fused to a pyridone ring. The presence of the 4-oxo and the 3-carboxylate groups is essential for the antibacterial activity. Substitutions on the quinolone ring, such as the trifluoromethyl group, can significantly affect the compound's biological activity and pharmacokinetic properties. The exact structure of Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate is not detailed in the provided papers, but it can be inferred that the trifluoromethyl groups would add to the lipophilicity and could potentially enhance the compound's ability to penetrate bacterial cell walls.

Chemical Reactions Analysis

Quinolone derivatives can undergo various chemical reactions, including nucleophilic addition, cyclocondensation, and cyclization, to yield a wide array of products. The reactivity of the quinolone carboxylate ester group allows for further functionalization and the introduction of various substituents at different positions on the quinolone core. These reactions are often used to synthesize novel derivatives with improved or unique antibacterial properties.

Physical and Chemical Properties Analysis

The physical and chemical properties of quinolone derivatives are influenced by their molecular structure. The introduction of fluorine atoms typically increases the compound's stability and lipophilicity, which can improve tissue penetration and bioavailability. The ester group in the 3-position is a common feature in prodrugs, which are converted to the active carboxylic acid form in vivo. The presence of the trifluoromethyl group in Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate would likely contribute to these properties, although specific data on this compound is not provided in the papers.

Scientific Research Applications

Synthesis and Derivative Formation

• Ethyl esters of various quinolinecarboxylic acids, including Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, have been synthesized for further chemical modifications. These modifications include intramolecular cyclization to form oxadiazinoquinoline derivatives (Nosova et al., 2002).
• Reactions involving nucleophilic addition and cyclocondensation have been performed on related compounds, leading to the creation of compounds with potential biological activity (Zahra et al., 2007).

Antibacterial Applications

• Certain derivatives of Ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate have shown significant antibacterial activity. For instance, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid demonstrated more activity than oxolinic acid against various bacteria (Koga et al., 1980).

Anticancer Research

• Modifications of ethyl 4-oxoquinoline-3-carboxylates have led to the development of compounds with moderate cytotoxic activity against cancer cell lines. For example, a derivative exhibited activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line (Regal et al., 2020).
• Synthesized derivatives of Ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylic acid showed significant anticancer activity against the MCF-7 breast cancer cell line (Gaber et al., 2021).

Safety And Hazards

This compound is classified as Aquatic Chronic 3 and Skin Sensitizer 1. It has a GHS07 pictogram and the signal word “Warning” is associated with it. The hazard statements for this compound are H317 - May cause an allergic skin reaction, and H412 - Harmful to aquatic life with long-lasting effects. The precautionary statements include P261 - Avoid breathing dust/fume/gas/mist/vapors/spray, P272 - Contaminated work clothing should not be allowed out of the workplace, P273 - Avoid release to the environment, P280 - Wear protective gloves/protective clothing/eye protection/face protection, P302 + P352 - IF ON SKIN: Wash with plenty of soap and water, and P333 + P313 - If skin irritation or rash occurs: Get medical advice/attention.

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