Cycloaddition reactions for antiviral compounds

Quadrelli, Paolo; Moiola, Mattia

doi:10.1016/b978-0-12-815273-7.00001-0

Cited by 5 publications

(4 citation statements)

References 182 publications

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“…In this POC study, we have synthesized the regioisomeric nucleosides 6a,b obtained through the chemistry of nitrosocarbonyl intermediates of type 1 , taking advantage of the use of the stable anthracenenitrile oxide 2 . The synthetic pathway relies upon a well-established protocol, setup in our laboratories and well-documented in several papers and reviews. , These methodologies are potentially suitable for introducing the phosphorus moiety needed for the biological tests on SARS-CoV-2 polymerases.…”

Section: Discussionmentioning

confidence: 99%

“…The synthetic pathway relies upon a well-established protocol, setup in our laboratories and well-documented in several papers and reviews. 12 , 13 These methodologies are potentially suitable for introducing the phosphorus moiety needed for the biological tests on SARS-CoV-2 polymerases.…”

Section: Discussionmentioning

confidence: 99%

“…For more than 20 years, we have been investigating the synthetic methodologies in organic chemistry to achieve reliable advancement in the knowledge of chemical structures apt to behave as antiviral compounds to contrast infectious diseases. 12 We strongly promoted the pericyclic reaction approach to several compounds and in particular the exploitation of the chemistry of nitrosocarbonyls, a family of fleeting intermediates suitable for the stereochemical ordinate introduction on carbocyclic scaffolds of functional groups suitable for the linear construction of purine and pyrimidine heterobases as well as introduction of phosphate units. 13 …”

Section: Introductionmentioning

confidence: 99%

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Inhibition of the RNA-Dependent RNA-Polymerase from SARS-CoV-2 by 6-Chloropurine Isoxazoline-Carbocyclic Monophosphate Nucleotides

Leusciatti,

Macchi,

Marino-Merlo

et al. 2023

ACS Omega

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Isoxazoline-carbocyclic monophosphate nucleotides were designed and synthesized through the chemistry of nitrosocarbonyl intermediates and stable anthracenenitrile oxide. Docking and molecular dynamics studies were first conducted for determining the best candidate for polymerase SARS-CoV-2 inhibition. The setup phosphorylation protocol afforded the nucleotides available for the biological tests. Preliminary inhibition and cytotoxicity assays were then performed, and the results showed a moderate activity of the nucleotides accompanied by cytotoxicity.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Inhibition of the RNA-Dependent RNA-Polymerase from SARS-CoV-2 by 6-Chloropurine Isoxazoline-Carbocyclic Monophosphate Nucleotides

Leusciatti,

Macchi,

Marino-Merlo

et al. 2023

ACS Omega

Self Cite

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“…The purpose of this manuscript is to furnish an overview of the chiral catalysts developed in recent years, highlighting the useful role of DAR in the synthesis of antiviral agents, endowing optical activity. Recently Quadrelli et al dedicated a chapter of a book to the cycloaddition reactions used for the synthesis of antiviral compounds [7], and a recent review described the biocatalytic routes applied to antiviral agents [8]. Taking into consideration our experience in the antiviral field [9][10][11][12][13][14][15][16][17][18] and in the application of DAR to the synthesis of antiviral agents [15,18] we were interested to investigate this topic in more detail.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Diels Alder Reaction: Application in the Synthesis of Antiviral Agents

Grillo

Bizzarri

2022

Catalysts

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The Diels–Alder reaction (DAR) is one of the most effective and reliable strategies for the construction of six-membered carbocyclic and heterocyclic rings, and it is widely used in the synthesis of organic molecules and drugs. Due to the high regio- and stereo-selectivity and its versatility, DARs have represented a powerful tool for organic chemistry for many years. In addition, the asymmetric DAR has become a fundamental synthetic approach in the preparation of optically active six-membered rings and natural compounds. The COVID-19-related pandemic requires continuous research; DAR represents an useful method to obtain optically active intermediates for the synthesis of antiviral agents under different catalytic conditions. We would like to highlight an intriguing synthetic procedure applied to the development of novel synthetic protocols that are potentially useful against a large panel of viruses and other unmet diseases.

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Heterocyclic compounds as antiviral drugs: Synthesis, structure–activity relationship and traditional applications

Santos

Martins

Bregadiolli

et al. 2021

Journal of Heterocyclic Chem

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A virus outbreak challenges the economic, medical, and public health infrastructure worldwide. More than one virus capable of triggering diseases have been identified per year since 1972, which requires the development of new ways of treatment and prevention, however, such processes are not rapid and easy. With the pandemic scenario experienced since early 2020, several drugs with well-known purposes have gained prominence, due to speculation of their use in the treatment against the new coronavirus. Among the main drugs studied, the vast majority contain a heterocyclic structure. In this review, we presented the traditional and efficient synthesis of 15 drugs that have been studied for the COVID-19 treatment, containing in their structure heterocycles like indole, quinoline, pyrimidone, tetrahydrofuran, pyrrolidine, triazole, pyridazine, pyrazole, pyrrolopyrimidine, azetidine, pyrrolotriazine, pyrazine, tetrahydropyran, benzofuran, spiroketal, and thiazole. Furthermore, we have shown the original applications, as well as their structure-activity relationship and what is their situation as a drug candidate against COVID-19. Thus, the objective was to consolidate the main synthetic and pharmacological aspects involving clinically developed heterocycles that at some point were presented as promising against SARS-CoV-2.

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Cycloaddition reactions for antiviral compounds

Cited by 5 publications

References 182 publications

Inhibition of the RNA-Dependent RNA-Polymerase from SARS-CoV-2 by 6-Chloropurine Isoxazoline-Carbocyclic Monophosphate Nucleotides

Inhibition of the RNA-Dependent RNA-Polymerase from SARS-CoV-2 by 6-Chloropurine Isoxazoline-Carbocyclic Monophosphate Nucleotides

Catalytic Enantioselective Diels Alder Reaction: Application in the Synthesis of Antiviral Agents

Heterocyclic compounds as antiviral drugs: Synthesis, structure–activity relationship and traditional applications

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