Abstract
Among heterocyclic compounds, quinoline is a privileged scaffold that appears as an important construction motif for the development of new drugs. Quinoline nucleus is endowed with a variety of therapeutic activities, and new quinolone derivatives are known to be biologically active compounds possessing several pharmacological activities. Many new therapeutic agents have been developed by using quinoline nucleus. Hence, quinoline and its derivatives form an important class of heterocyclic compounds for the new drug development. Numerous synthetic routes have been developed for the synthesis of quinoline and its derivatives due to its wide range of biological and pharmacological activities. The article covers the synthesis as well as biological activities of quinoline derivatives such as antimalarial, anticancer, antibacterial, anthelmintic, antiviral, antifungal, anti-inflammatory, analgesic, cardiovascular, central nervous system, hypoglycemic, and miscellaneous activities.
Keywords
- quinoline
- heterocyclic compound
- quinoline derivatives
- synthesis
- biological activity
1. Introduction
Quinoline
Quinoline moiety commonly exists in various natural compounds (
2. Synthesis
In the literature, a number of established protocols have been reported for the synthesis of quinoline ring, which can be altered to produce a number of differently substituted quinolines. The quinoline ring has been generally synthesized by various conventional named reactions such as Skraup, Doebner-Von Miller, Pfitzinger, Friedlander, Conrad-Limpach, and Combes synthesis (Figure 1) [1].
Apart from the conventional methods, a vast number of synthetic routes have been developed for the synthesis of quinoline and quinoline derivatives. Chen et al. reported the synthesis of 2,4-disubstituted quinolines,
2,4-Disubstituted quinolones,
2,4-Diphenyl-2-methyl-1,2-dihydroquinoline,
2,3,4-Trisubstituted quinolones,
By stirring 2-aminoaryl ketones and various α-methylene ketones in the presence of dodecylphosphonic acid (DPA) catalyst in water or solvent-free conditions, poly-substituted quinolones,
2-Aminobenzyl alcohol reacts with ketones or alcohols in the presence of a base, and benzophenone resulted in the formation of poly-substituted quinolones,
Horn et al. reported the synthesis of quinolines,
3,4-Dihydroquinolin-2-ones,
Wang et al. developed a method for the synthesis of 2-phenylquinoline-4-carboxylic acids,
Kouznetsov et al. synthesized phenyl-substituted quinolones,
Wang et al. reported the synthesis of 2-phenyl-4-alkoxy quinolines,
Two molecules of
A one-pot reaction of 2-aminoaryl ketones with certain arylacetylenes results in the formation of 2,4-disubstituted quinolones,
Kowsari et al. synthesized certain quinolones,
1,4-Diazabicyclo[2.2.2]octane (DABCO) promoted structurally diverse 2-alkoxy- and 2-aryloxy-3-substituted quinolones,
Benzimidoyl chlorides when treated with 1-(1-(allyloxy)prop-2-ynyl)benzene (1,6-enynes) yielded diverse quinoline derivatives,
Diversified quinolones,
3. Biological activity
3.1 Antimalarial
Quinolines are known for their excellent antimalarial properties. Raynes et al. developed bisquinolines,
3.2 Anti-inflammatory activity
A quinoline derivative,
3.3 Analgesic activity
4-Substituted-7-trifluoromethylquinolines
3.4 Antibacterial
Ma et al. reported the synthesis and antibacterial evaluation of phenoxy-, phenylthio-, and benzyloxy-substituted quinolones,
3.5 Antitumor
Some amido-anilinoquinolines,
3.6 Antifungal
Certain tetrahydroquinolines,
3.7 Antiviral
Several mono- and poly-substituted quinolones,
3.8 Anthelmintic
Substituted 2,4-arylquinolines,
3.9 Antiprotozoal
2-Propyl quinoline and 2-(3-methyloxiran-2-yl)quinoline alkaloids
3.10 Cardiovascular activity
Srimal et al. demonstrated the hypotensive activity of centhaquin,
3.11 Reproductive system
Tetrahydroquinolines,
3.12 Miscellaneous
Quinolines and quinoline derivatives possess a number of miscellaneous biological activities also. Evans et al. synthesized few quinolones,
4. Conclusion
Since quinoline and its derivatives are known for their wide spectrum of pharmacological activities, a number of synthetic methods have been developed from time to time for their synthesis by conventional, homogeneous, and heterogeneous acid-catalyzed methods; rare-earth-catalyzed, transition metal-catalyzed, radical-catalyzed, microwave-assisted, ultrasound-promoted, or solvent-free conditions, and many more. This book chapter will be very useful to the researcher working in this field, and it would help them to develop new synthetic methods for the potent quinoline derivatives with good or enhanced biological activities for the future.
Acknowledgments
The author is grateful to DST-SERB for the Early Career Research Award grant (ECR/2016/001041). The author is thankful to SASTRA Deemed University, Thanjavur, for their encouragement and support.
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