The contemporary synthetic recipes to access versatile quinoline heterocycles

Matada, Basavarajaiah Suliphuldevara; Yernale, Nagesh Gunavanthrao

doi:10.1080/00397911.2021.1876240

Cited by 18 publications

(10 citation statements)

References 72 publications

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“…The Quinoline ring is a multi bio-active moiety that belongs to the quinine group involved in various drug syntheses and the wellknown antimalarial drug. The classical quinoline synthesis is through Skraup synthesis, which has some drawbacks (Radhakrishna et al, 2017;Basavarajaiah and Nagesh, 2021). MOF-199 has been used as an efficient, recyclable catalyst in esterification, Ullmann-type coupling, and oxidative dehydrogenation reactions.…”

Section: Cu (Ii) Basedmentioning

confidence: 99%

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

Gangu

Jonnalagadda

2021

Front. Chem.

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Metal-organic frameworks (MOFs) have emerged as versatile candidates of interest in heterogeneous catalysis. Recent research and developments with MOFs positively endorse their role as catalysts in generating invaluable organic compounds. To harness the full potential of MOFs in value-added organic transformation, a comprehensive look at how these materials are likely to involve in the catalytic processes is essential. Mainstays of MOFs such as metal nodes, linkers, encapsulation materials, and enveloped structures tend to produce capable catalytic active sites that offer solutions to reduce human efforts in developing new organic reactions. The main advantages of choosing MOFs as reusable catalysts are the flexible and robust skeleton, regular porosity, high pore volume, and accessible synthesis accompanied with cost-effectiveness. As hosts for active metals, sole MOFs, modified MOFs, and MOFs have made remarkable advances as solid catalysts. The extensive exploration of the MOFs possibly led to their fast adoption in fabricating new biological molecules such as pyridines, quinolines, quinazolinones, imines, and their derivatives. This review covers the varied MOFs and their catalytic properties in facilitating the selective formation of the product organic moieties and interprets MOF’s property responsible for their elegant performance.

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Section: Cu (Ii) Basedmentioning

confidence: 99%

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

Gangu

Jonnalagadda

2021

Front. Chem.

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“…The biological importance of quinoline-based drugs has resulted in the synthesis of this substituted heterocycle becoming a hot topic for organic chemists worldwide [ 38 , 39 , 40 , 41 ]. A plethora of elegant syntheses have been developed; however, the use of harsh conditions and limitations due to the nature of some reagents have restricted the application of these protocols both in academia and in industry [ 42 ]. The recent trend of obtaining targets with high purity using sustainable conditions has resulted in the use of metal catalysts becoming central in the synthetic strategies of complex drugs.…”

Section: Chloroquine and Hydroxychloroquinementioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

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The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus.

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“…The following reagents were used in the reaction (Figure 1 The mechanism of the general reaction for obtaining PHQs derivatives (13) begins with the removal of an α-hydrogen from dimedone by a base, forming an enolate ion that has an area of a high concentration negative charge on the α-carbon. This compound is stabilized by the resonance between the electron pairs and the carbonyl groups bonded to the carbon.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

“…23 MHz for 1H frequency) with an Ultrashield Plus® magnet. The spectrometer is equipped with a 5 mm TCI (Triple Resonance Inverse) CryoProbe -1 H and 13 C nuclei-and cold preamplifiers (temperature at approximately 77K). The probe has a Z-Gradient (53G/cm) and an Automatic Tuning and Matching accessory (ATMA).…”

Section: Characterization By Nuclear Magnetic Resonance (Nmr)mentioning

confidence: 99%

“…Therefore, the objective in the present work was to carry out the multicomponent reaction of a PHQ derivative and perform its structural characterization using the Fourier transform infrared spectroscopy (FTIR) and 1 H-and 13 C-nuclear magnetic resonance (NMR). In addition, the biological activities exerted by the synthesized compound were also evaluated (antimicrobial activity and modulatory potential on enzymes that act in hemostatic and inflammatory processes).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of the Polyhydroquinoline Derivative 4-(2-Chloro-Phenyl)-2,7,7-Trimethyl5-oxo-1,4,5,6,7,8-Hexahydroquinoline-3-Carboxylic Acid Ethyl Ester: Antimicrobial and Enzyme Modulator

Machado

Trento

Pinelli

et al. 2021

Preprint

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Multicomponent reactions are extremely relevant in green chemistry. They offer better conditions than traditional synthesis and are, therefore, used for many organic modifications. Recently, the synthesis of polyhydroquinolines has received much attention for its high pharmacological potential. In the present study, a polyhydroquinoline derivative was synthesized without the use of catalysts or solvents. The results of nuclear magnetic resonance and infrared spectroscopy demonstrated that the molecule was successfully synthesized. The molecule presents significant results of antimicrobial activity for the bacteria tested in the serial dilution method. It also increased the clotting time by 25.66 seconds for the highest dose and 12.66 seconds for the other doses tested. Prior incubation with the dose of 125 mg reduced the thrombolytic activity to 73%. The 125, 100, and 50 mg doses previously incubated with Bothrops moojeni venom inhibited approximately 30% of the phospholipase activity. The molecule was also able to reduce the cytotoxicity induced by proteases significantly. In conclusion, the molecule presents several biological properties, which highlights its pharmaceutical potential.

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The contemporary synthetic recipes to access versatile quinoline heterocycles

Cited by 18 publications

References 72 publications

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

Synthesis of the Polyhydroquinoline Derivative 4-(2-Chloro-Phenyl)-2,7,7-Trimethyl5-oxo-1,4,5,6,7,8-Hexahydroquinoline-3-Carboxylic Acid Ethyl Ester: Antimicrobial and Enzyme Modulator

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