93107-30-3 | 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

CAS:93107-30-3 | 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid,Description

Synthesis Analysis

The synthesis of related quinolone derivatives involves multiple steps, including acyl-chlorination, condensation, decarboxylation, esterification, cyclopropylamine replacement, and cyclization processes. For instance, Liu Zhe reported the preparation of a closely related compound, 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-ethyl carboxylate, with an overall yield of 48% starting from 3-methoxyl-2,4,5-trifluorobenzoic acid (Liu Zhe, 2001).

Molecular Structure Analysis

Molecular structure analyses, including infrared spectra and Fourier-transform ion cyclotron resonance spectrometry (FT-ICR-MS), provide insights into the characteristic fragment ions and the structural confirmation of quinolone derivatives. Zhiwei Lin conducted a study focusing on a similar quinolone derivative, highlighting the utility of these techniques in understanding the molecular structure (Lin, 2014).

Chemical Reactions and Properties

Quinolone derivatives undergo various chemical reactions, including displacement reactions with amine nucleophiles, which occur regioselectively at specific positions depending on the substrate and solvent. Shibamori et al. demonstrated this regioselectivity in the synthesis of quinolone derivatives, allowing for the introduction of different nucleophiles at desired positions (Shibamori et al., 1990).

Physical Properties Analysis

The study of physical properties such as melting and dissociation characteristics is essential for understanding the behavior of quinolone derivatives in various conditions. Yin Qiuxiang investigated these properties for a related compound, providing valuable data for the crystallization and purification processes in the industrial manufacture of quinolone antibiotics (Yin Qiuxiang, 2002).

Chemical Properties Analysis

The chemical properties of quinolone derivatives, including their reactivity and interaction with other molecules, are crucial for their potential applications. Photochemistry studies, for example, reveal how these compounds behave under irradiation, which is pertinent for their stability and efficacy. M. Mella, E. Fasani, and A. Albini explored the photochemical behavior of ciprofloxacin, a well-known quinolone derivative, in aqueous solutions, providing insights into its photostability and reaction mechanisms (Mella, Fasani, & Albini, 2001).

Scientific Research Applications

• Synthesis and Antibacterial Activity :
  • Novel fluoroquinolones with potent in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis, including multi-drug resistant strains (Senthilkumar et al., 2009).
  • Various 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid derivatives showing significant antibacterial activity, including against gram-positive and gram-negative bacteria (Miyamoto et al., 1990).
• Pharmacokinetics and Stability :
  • Pharmacokinetic properties in animals of a specific derivative, AT-4140, characterized by good tissue penetration and a long half-life in plasma and tissues (Nakamura et al., 1990).
  • Photochemical stability and reactions of a related compound, ciprofloxacin, in various conditions, highlighting the importance of understanding the photostability of these compounds (Mella et al., 2001).
• Analytical Methods :
  • Development of an RP-HPLC method for determining concentrations of a related compound, demonstrating the importance of analytical techniques in quality control of these substances (Fu Yan-wen, 2008).
• Synthetic Routes and Chemical Properties :
  • Exploration of different synthetic routes and the preparation of various derivatives, which is crucial for the development of new pharmaceutical compounds (Egawa et al., 1987).
  • Investigation of melting and dissociation properties of related compounds, important for understanding their physical and chemical behavior in pharmaceutical formulations (Yin Qiuxiang, 2002).

Safety And Hazards

This compound is suspected of damaging fertility or the unborn child and is harmful to aquatic life with long-lasting effects. It is advised to avoid breathing mist, gas, or vapors, and to avoid contact with skin and eyes. Use of personal protective equipment, including chemical impermeable gloves, is recommended.

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