• 1. 1123. Preparation and nuclear magnetic resonance spectra of some halogenoquinolines. Nearly degenerate ABX spectra
  C. W. Haigh,M. H. Palmer,B. Semple J. Chem. Soc. 1965 6004
• 2. 559. Quinaldine and 4-hydroxyquinaldine derivatives from m-chloroaniline and m-toluidine
  A. M. Spivey,F. H. S. Curd J. Chem. Soc. 1949 2656
• 3. 875. Physical properties and chemical constitution. Part XXXVI. The electric dipole moments of phenyl derivatives of some N-heterocyclic molecules
  C. W. N. Cumper,R. F. A. Ginman,A. I. Vogel J. Chem. Soc. 1962 4518
• 4. 710. The Skraup reaction. Formation of 5- and 7-substituted quinolines
  M. H. Palmer J. Chem. Soc. 1962 3645

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Chloroquinolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Haloquinolines Chloroquinolines

Introduction to 5-Chloroquinaldine (CAS No. 4964-69-6)

5-Chloroquinaldine, identified by the chemical compound code CAS No. 4964-69-6, is a significant heterocyclic organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the quinaldine family, characterized by a fused benzene and pyridine ring system, with a chlorine substituent at the 5-position. The unique structural and electronic properties of 5-Chloroquinaldine make it a versatile intermediate in the synthesis of various pharmacologically active molecules, particularly those targeting infectious diseases and metabolic disorders.

The synthesis of 5-Chloroquinaldine typically involves the chlorination of quinaldine or its derivatives, a process that requires precise control over reaction conditions to ensure high yield and purity. The presence of the chlorine atom at the 5-position enhances the electrophilicity of the ring system, facilitating further functionalization through nucleophilic substitution or coordination with metal catalysts. This reactivity has been exploited in multiple synthetic pathways, including cross-coupling reactions that introduce aryl or heteroaryl groups, expanding the structural diversity of derivatives.

In recent years, 5-Chloroquinaldine has been explored as a key precursor in the development of novel antimicrobial agents. The growing threat of antibiotic-resistant pathogens has spurred research into structurally novel compounds that can disrupt essential bacterial processes. Studies have demonstrated that derivatives of 5-Chloroquinaldine exhibit potent activity against Gram-positive and Gram-negative bacteria, as well as certain fungal species. The mechanism of action often involves interference with bacterial DNA gyrase or RNA polymerase, critical enzymes for bacterial replication and transcription.

Moreover, the structural framework of 5-Chloroquinaldine has been leveraged in the design of compounds targeting human diseases beyond infections. For instance, its scaffold has been modified to develop potential inhibitors of kinases and other enzymes implicated in cancer progression. The chlorine substituent at the 5-position serves as a handle for further derivatization, allowing chemists to fine-tune physicochemical properties such as solubility, bioavailability, and target specificity. Preclinical studies have shown promising results with certain 5-Chloroquinaldine derivatives in animal models of cancer, highlighting their therapeutic potential.

The role of computational chemistry in optimizing 5-Chloroquinaldine-based drug candidates cannot be overstated. Advanced molecular modeling techniques have enabled researchers to predict binding affinities and metabolic stability with high accuracy. By integrating experimental data with computational predictions, scientists can rapidly screen large libraries of derivatives to identify lead compounds with optimal pharmacokinetic profiles. This approach has significantly accelerated the drug discovery pipeline for 5-Chloroquinaldine-derived molecules.

Recent advancements in synthetic methodologies have also contributed to the growing interest in 5-Chloroquinaldine. Transition-metal-catalyzed reactions, such as palladium-mediated cross-coupling and copper-assisted cyclizations, have provided efficient routes to complex derivatives while minimizing byproduct formation. These innovations have not only improved yields but also opened new avenues for structural diversification, enabling the exploration of previously inaccessible chemical space.

The pharmacological evaluation of 5-Chloroquinaldine derivatives has revealed intriguing interactions with biological targets beyond traditional antimicrobial applications. For example, certain analogs have demonstrated neuroprotective effects in preclinical models by modulating calcium signaling pathways or inhibiting oxidative stress-induced neuronal damage. Such findings underscore the compound's potential utility in neurodegenerative disorders like Alzheimer's disease and Parkinson's disease. Further investigation into these mechanisms could pave the way for novel therapeutic strategies.

In conclusion, 5-Chloroquinaldine (CAS No. 4964-69-6) represents a valuable scaffold in medicinal chemistry due to its structural versatility and functional reactivity. Ongoing research continues to uncover new applications for this compound and its derivatives across diverse therapeutic areas. As synthetic methodologies advance and computational tools become more sophisticated, the future prospects for 5-Chloroquinaldine-based therapeutics appear increasingly promising.

• 64383-53-5(Benzo[h]quinoline, 7,10-dichloro-2-methyl-)
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• 6127-16-8(4-chloro-2-methyl-1H-Indole)
• 4965-33-7(7-Chloroquinaldine)
• 4295-06-1(4-Chloro-2-methylquinoline)
• 886362-21-6(4,6-Dichloro-2-methyl-1H-indole)
• 61773-04-4(Benzo[h]quinoline, 4-chloro-2-methyl-)
• 71063-11-1(Quinoline, 5,6-dichloro-2-methyl-)