196603-96-0 | 4-(4-Bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline

CAS:196603-96-0 | 4-(4-Bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline,Description

This compound is part of the quinazoline derivatives, a class of heterocyclic aromatic organic compounds. Quinazolines have attracted significant attention due to their diverse pharmacological properties, including antitumor, antibacterial, and kinase inhibition activities. The specific structure of "4-((4-Bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-ol" suggests its potential utility in developing therapeutic agents, particularly in targeting various cancer types by inhibiting tyrosine kinase enzymes.

Synthesis Analysis

The synthesis of quinazoline derivatives like "4-((4-Bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-ol" typically involves multi-step chemical reactions, starting from simple precursors. For instance, a key intermediate for vandetanib, which antagonizes the vascular endothelial growth factor receptor (VEGFR) and the epidermal growth factor receptor (EGFR), was obtained from 4-hydroxy-3-methoxybenzoic acid through several steps, yielding an overall 42.6% (Li Rong-dong, 2011).

Molecular Structure Analysis

The molecular structure of quinazoline derivatives is crucial for their biological activity. The crystal structure analysis, such as X-ray crystallography, helps in understanding the molecular conformation, which is essential for binding to biological targets. The detailed molecular structure, including bond lengths, angles, and conformation, provides insights into the compound's interaction with biological molecules, influencing its pharmacological profile.

Chemical Reactions and Properties

Quinazoline derivatives undergo various chemical reactions, including nucleophilic substitutions, which are fundamental in modifying their chemical structure for enhanced biological activity. The reactivity of the bromo and fluoro substituents on the phenyl ring can be exploited to introduce additional functional groups, tailoring the compound's properties for specific biological targets.

Physical Properties Analysis

The physical properties of "4-((4-Bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-ol," such as solubility, melting point, and stability, are crucial for its application in drug formulation. These properties are determined by its molecular structure and significantly affect the compound's bioavailability and pharmacokinetics.

Chemical Properties Analysis

The chemical stability, reactivity, and interaction with biological molecules define the compound's chemical properties. These properties are influenced by the presence of the bromo and fluoro groups, which affect the electron distribution within the molecule, thereby influencing its reactivity and biological activity.

For further details and a comprehensive understanding of the compound's synthesis, structure, and properties, the referenced scientific literature provides in-depth insights:

• (Li Rong-dong, 2011)

Scientific Research Applications

1. Fluorescent Probes for Biological Applications

• Summary of Application: Fluorescent probes based on the bimane scaffold have been developed for a broad range of biological applications. These probes have tunable absorption and emission in the visible region with large Stokes shifts.
• Methods of Application: The probes featuring electron-donating groups exhibit rotor effects that are sensitive to polarity and viscosity by “intramolecular charge transfer” (ICT) and twisted intramolecular charge transfer (TICT) mechanisms.
• Results or Outcomes: These properties enable their application as “turn-on” fluorescent probes to detect fibrillar aggregates of the α-synuclein (αS) protein that are a hallmark of Parkinson’s disease (PD). One probe shows selective binding to αS fibrils relative to soluble proteins in cell lysates and amyloid fibrils of tau and amyloid-β.

2. Functional Carbohydrates Production

• Summary of Application: The book provides an overview of the development of functional carbohydrate-related enzymes in food enzyme. It includes the research on the isomerases or epimerases involved in the production of rare sugars.
• Methods of Application: The book summarizes the new enzymatic technologies and applications in the functional carbohydrate field.
• Results or Outcomes: The book provides an overview of the development of functional carbohydrate-related enzymes in food enzyme.

More Information