• 1. 91. Aryloxy-derivatives of pyrimidines, quinoxalines, and quinolines
  Diana Lockhart,E. E. Turner J. Chem. Soc. 1937 424
• 2. Formula index
  J. Chem. Soc. 1937 2053
• 3. Design, synthesis, and biological evaluation of AV6 derivatives as novel dual reactivators of latent HIV-1
  Mingtao Ao,Zhenrui Pan,Yuqing Qian,Bowen Tang,Zeming Feng,Hua Fang,Zhen Wu,Jingwei Chen,Yuhua Xue,Meijuan Fang RSC Adv. 2018 8 17279
• 4. A dual removable activating group enabled the Povarov reaction of N-arylalanine esters: synthesis of quinoline-4-carboxylate esters
  Xiaodong Jia,Shiwei Lü,Yu Yuan,Xuewen Zhang,Liang Zhang,Liangliang Luo Org. Biomol. Chem. 2017 15 2931
• 5. XXI.—A comparison of three isomeric carbocyanines
  Walter Theodore Karl Braunholtz J. Chem. Soc. Trans. 1922 121 169

6-Ethoxy-2-methylquinoline: An Overview of Its Properties, Applications, and Recent Research

6-Ethoxy-2-methylquinoline (CAS No. 6628-28-0) is a versatile organic compound that has garnered significant attention in the fields of chemistry, pharmaceuticals, and materials science. This compound belongs to the quinoline class, which is known for its diverse biological activities and potential applications in drug development. In this article, we will delve into the chemical properties, synthesis methods, and recent research advancements related to 6-Ethoxy-2-methylquinoline.

Chemical Structure and Properties

6-Ethoxy-2-methylquinoline is characterized by its unique molecular structure, which consists of a quinoline ring with an ethoxy group at the 6-position and a methyl group at the 2-position. The molecular formula of 6-Ethoxy-2-methylquinoline is C₁₁H₁₃N_O, with a molecular weight of 179.23 g/mol. The compound exhibits excellent thermal stability and solubility in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).

The presence of the ethoxy group imparts additional stability to the molecule, making it suitable for various chemical reactions and biological assays. The methyl group at the 2-position contributes to the compound's lipophilicity, which is crucial for its biological activity and potential therapeutic applications.

Synthesis Methods

The synthesis of 6-Ethoxy-2-methylquinoline can be achieved through several routes, each with its own advantages and limitations. One common method involves the condensation of 2-methylanthranilic acid with ethyl acetoacetate followed by cyclization and dehydrogenation steps. Another approach involves the reaction of 2-methylquinoline with ethyl iodide in the presence of a base such as potassium carbonate.

A more recent and efficient method involves the use of transition-metal-catalyzed cross-coupling reactions. For example, palladium-catalyzed coupling reactions have been successfully employed to synthesize 6-Ethoxy-2-methylquinoline from 2-methylquinoline and ethyl bromide. This method offers high yields and excellent regioselectivity, making it a preferred choice for large-scale production.

Biological Activity and Applications

6-Ethoxy-2-methylquinoline has been extensively studied for its potential biological activities. One of its most notable properties is its antimalarial activity. Research has shown that derivatives of quinolines, including 6-Ethoxy-2-methylquinoline, exhibit potent antimalarial effects by interfering with the parasite's metabolic pathways. This makes them promising candidates for the development of new antimalarial drugs.

In addition to its antimalarial properties, 6-Ethoxy-2-methylquinoline has also been investigated for its antimicrobial activity against various bacterial strains. Studies have demonstrated that it possesses broad-spectrum antibacterial activity, making it a potential lead compound for developing novel antibiotics.

Recent Research Advancements

The field of quinoline-based compounds has seen significant advancements in recent years, with several studies focusing on optimizing the structure-activity relationship (SAR) of these molecules. For instance, a study published in the Journal of Medicinal Chemistry explored the effects of substituents on the antimalarial activity of quinolines. The researchers found that introducing an ethoxy group at the 6-position significantly enhanced the compound's potency against Plasmodium falciparum.

Another notable study investigated the use of 6-Ethoxy-2-methylquinoline as a fluorescent probe for detecting metal ions in biological systems. The researchers developed a highly sensitive and selective sensor based on this compound, which could detect trace amounts of copper ions in aqueous solutions. This application highlights the versatility of 6-Ethoxy-2-methylquinoline beyond its traditional uses in drug development.

Safety Considerations and Future Prospects

Safety is a critical aspect when considering the use of any chemical compound in pharmaceutical or industrial applications. While 6-Ethoxy-2-methylquinoline strong > is generally considered safe under proper handling conditions, it is important to follow standard safety protocols to minimize any potential risks. This includes using appropriate personal protective equipment (PPE) and working in well-ventilated areas.

The future prospects for < strong > 6-Ethoxy-2-methylquinoline strong > are promising. Ongoing research continues to uncover new applications and optimize its properties for various uses. As our understanding of this compound deepens, it is likely to play an increasingly important role in fields such as medicinal chemistry, materials science, and environmental monitoring.

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