Microwave irradiation for the synthesis of quinoline scaffolds: a review

Tople, Manesh S.; Patel, Navin B.; Patel, Parth P.

doi:10.1007/s13738-022-02648-y

Cited by 6 publications

(5 citation statements)

References 83 publications

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“…The quinoline derivatives are present in various natural species, principally in alkaloids; for example, quinine was extracted from the bark of the Cinchona tree in 1820 and was used to cure malaria. Several conventional and microwave irradiation reactions have been developed to obtain quinoline derivatives (for example, the Skraup, Doebner, Doebner Miller, Pfitzinger, Gauld Jacobs, Riehm, Combes, Conard–Limpach and Povarov reactions); moreover, some drugs containing quinoline scaffolds (such as quinine, cinchonine, amodiaquine, ciprofloxacin, topotecan, mefloquine, and pelitinib) present anti-malarial, anti-bacterial, anti-inflammatory, anti-microbial, anti-cancer, anti-tubercular, and anti-HIV activities [ 72 ].…”

Section: Quinolinementioning

confidence: 99%

The Application of Microwaves, Ultrasounds, and Their Combination in the Synthesis of Nitrogen-Containing Bicyclic Heterocycles

Frecentese

Sodano

Corvino

et al. 2023

IJMS

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The use of alternative energy sources, such as microwaves (MW) or ultrasounds (US), and their mutual cross-combination have been widely described in the literature in the development of new synthetic methodologies in organic and medicinal chemistry. In this review, our attention is focused on representative examples, reported in the literature in the year range 2013–2023 of selected N-containing bicyclic heterocycles, with the aim to highlight the advantages of microwave- and ultrasound-assisted organic synthesis.

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Section: Quinolinementioning

confidence: 99%

The Application of Microwaves, Ultrasounds, and Their Combination in the Synthesis of Nitrogen-Containing Bicyclic Heterocycles

Frecentese

Sodano

Corvino

et al. 2023

IJMS

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“…The involvement of base‐promoted condensation reactions and transition metal‐catalyzed coupling reactions is crucial in the synthesis of quinazoline. However, the topic of multicomponent reactions is beyond the scope of this section [199–203] …”

Section: Quinazolinesmentioning

confidence: 99%

“…However, the topic of multicomponent reactions is beyond the scope of this section. [199][200][201][202][203]…”

Section: Synthetic Strategies Of Quinazolinementioning

confidence: 99%

Six‐Membered Aromatic Nitrogen Heterocyclic Anti‐Tumor Agents: Synthesis and Applications

Li,

Gu,

Nong

et al. 2023

The Chemical Record

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Cancer stands as a serious malady, posing substantial risks to human well‐being and survival. This underscores the paramount necessity to explore and investigate novel antitumor medications. Nitrogen‐containing compounds, especially those derived from natural sources, form a highly significant category of antitumor agents. Among these, antitumor agents with six‐membered aromatic nitrogen heterocycles have consistently attracted the attention of chemists and pharmacologists. Accordingly, we present a comprehensive summary of synthetic strategies and clinical implications of these compounds in this review. This entails an in‐depth analysis of synthesis pathways for pyridine, quinoline, pyrimidine, and quinazoline. Additionally, we explore the historical progression, targets, mechanisms of action, and clinical effectiveness of small molecule inhibitors possessing these structural features.

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“…By using different aromatic amines and b-ketoesters, the reaction can be modified to yield various substituted quinoline derivatives with different functional groups and substitution patterns. [9][10][11] Mechanistic studies have been carried out to understand the reaction mechanism and identify key intermediates. Despite its usefulness, the Conard-Limpach synthesis has some limitations.…”

Section: Fig 4 Knorr Quinoline Synthesismentioning

confidence: 99%

“…Additionally, the reaction's selectivity and yield may be affected by factors such as pH and the nature of the catalyst used. Nonetheless, the method's versatility in producing substituted quinoline derivatives and its role in advancing scientific research make it an important synthetic pathway in organic chemistry 3,10,11 .…”

Section: Fig 4 Knorr Quinoline Synthesismentioning

confidence: 99%

From Molecules to Medicine: The Remarkable Pharmacological Odyssey of Quinoline and It's Derivatives

Panchal¹,

Vaghela²

2023

Orient. J. Chem

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Quinoline, a nitrogen-containing heterocyclic molecule, has emerged as an important scaffold in medicinal chemistry due to its diverse pharmacological effects. The fused quinazoline nucleus in particular has garnered attention for its potent properties, including antibacterial, antiviral, anti-cancer, anti-inflammatory, antioxidant, and anticonvulsant effects. The mechanism of action of these quinoline derivatives is specific to their pharmacological activity. Researchers have studied the chemical and pharmacological properties of quinoline derivatives extensively, with a focus on their anticancer activity. Their ability to bind with DNA, impede DNA synthesis, and cause oxidative stress has made them promising candidates for cancer therapy. The quinoline nucleus's unique chemical structure and flexibility of substituents provide a vital component in drug discovery research. This review article provides a comprehensive synthesis of the chemical and pharmacological properties of quinoline derivatives. The study highlights the immense potentiality of this ring system and their pharmacological scaffold. The review covers the diverse biological activity of quinoline derivatives and their mechanism of action, including their effects on DNA synthesis, cell division, virus replication, adhesion to host cells, cytokine generation, gene modulation, free radical scavenging, and neurotransmitter activation. The ability to modify the quinoline nucleus with different substituents around the centroid has made it a privileged scaffold for researchers to work with. Researchers have created novel therapeutic compounds with improved pharmacological characteristics, leading to innovative therapies for various disorders. Further research into synthesis, reactions, and pharmacological effects of quinoline derivatives can pave the way for the development of new drugs. The article specifically focuses on the anticancer activity of quinoline derivatives, highlighting their potential as a viable clinical candidate for cancer therapy. The review emphasizes the importance of the quinoline nucleus as a key scaffold for drug discovery research and encourages further exploration of its chemical and pharmacological properties. In conclusion, this review article provides a comprehensive overview of the immense potential of quinoline derivatives and their significance in medicinal chemistry research.

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Microwave irradiation for the synthesis of quinoline scaffolds: a review

Cited by 6 publications

References 83 publications

The Application of Microwaves, Ultrasounds, and Their Combination in the Synthesis of Nitrogen-Containing Bicyclic Heterocycles

The Application of Microwaves, Ultrasounds, and Their Combination in the Synthesis of Nitrogen-Containing Bicyclic Heterocycles

Six‐Membered Aromatic Nitrogen Heterocyclic Anti‐Tumor Agents: Synthesis and Applications

From Molecules to Medicine: The Remarkable Pharmacological Odyssey of Quinoline and It's Derivatives

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