Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Hu, Yaping; Chen, Binfeng; Lei, Zaiqiang; Zhao, Hongqian; Zhu, He; Quan, Peng; Tian, Yuan

doi:10.3390/molecules24112176

Cited by 6 publications

(3 citation statements)

References 30 publications

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“…I. verum is the main industrial source of shikimic acid. Shikimic acid is the primary ingredient of oseltamivir phosphate, which serves as neuraminidase inhibitor and is the effective antiviral drug for the treatment and prevention of influenza (Hu et al, 2019). Lonicera japonica Thunb.…”

mentioning

confidence: 99%

The Inhibitory Activities and Antiviral Mechanism of Medicinal Plant Ingredient Quercetin Against Grouper Iridovirus Infection

Liu

Xiao

et al. 2020

Front. Microbiol.

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Singapore grouper iridovirus (SGIV) causes high mortality rates in mariculture, and effective treatments against SGIV infection are urgently required. Illicium verum Hook. f. (I. verum) is a well-known medicinal plant with a variety of biological activities. The natural ingredient quercetin isolated from I. verum could effectively inhibit SGIV infection in a dose-dependent manner. The possible antiviral mechanism of quercetin was further analyzed in this study. It showed that quercetin did obvious damages to SGIV particles. Furthermore, quercetin could interfere with SGIV binding to targets on host cells (by 76.14%), disturb SGIV invading into host cells (by 56.03%), and effect SGIV replication in host cells (by 52.73%), respectively. Quercetin had the best antiviral effects during the SGIV life cycle of binding to the receptors on host cells' membranes. Overall, the results suggest that quercetin has direct and host-mediated antiviral effects against SGIV and holds great potential for developing effective drugs to control SGIV infection in aquaculture.

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mentioning

confidence: 99%

The Inhibitory Activities and Antiviral Mechanism of Medicinal Plant Ingredient Quercetin Against Grouper Iridovirus Infection

Liu

Xiao

et al. 2020

Front. Microbiol.

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“…The amino group in 85 was further elaborated to the guanidino group by treatment with 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine to afford GOC-sulfonamides 86 after the removal of the Boc groups. The compound 86 exhibited high inhibitory activity against the H1N1 influenza virus, with the final yield of the product being 39% [123,124].…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

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Among the variety of sulfonamides, triflamides (CF3SO2NHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of N-trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CF3SO2)2NH, Tf2NH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel–Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.

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“…61 Hydrolysis: Oseltamivir was metabolized to GS4071, (3R,4R,5S)-3-(1-ethylpropyloxy)-4-acetamido-5-aminocyclohexene-1-carboxylate (an active neuraminidase inhibitor) through ester hydrolysis. 59 Conjugation: Arbidol was conjugated with glucuronide and sulfate via free hydroxyl groups on the indole ring by UGT1A9. 64 The obtained conjugates were major metabolites in human urine.…”

Section: Metabolic Reaction Of Nn-avdsmentioning

confidence: 99%

Antiviral Drug Delivery System for Enhanced Bioactivity, Better Metabolism and Pharmacokinetic Characteristics

Chen¹,

Wang²,

Song³

et al. 2021

IJN

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Antiviral drugs (AvDs) are the primary resource in the global battle against viruses, including the recent fight against corona virus disease 2019 . Most AvDs require multiple medications, and their use frequently leads to drug resistance, since they have poor oral bioavailability and low efficacy due to their low solubility/low permeability. Characterizing the in vivo metabolism and pharmacokinetic characteristics of AvDs may help to solve the problems associated with AvDs and enhance their efficacy. In this review of AvDs, we systematically investigated their structure-based metabolic reactions and related enzymes, their cellular pharmacology, and the effects of metabolism on AvD pharmacodynamics and pharmacokinetics. We further assessed how delivery systems achieve better metabolism and pharmacology of AvDs. This review suggests that suitable nanosystems may help to achieve better pharmacological activity and pharmacokinetic behavior of AvDs by altering drug metabolism through the utilization of advanced nanotechnology and appropriate administration routes. Notably, such AvDs as ribavirin, remdesivir, favipiravir, chloroquine, lopinavir and ritonavir have been confirmed to bind to the severe acute respiratory syndrome-like coronavirus (SARS-CoV-2) receptor and thus may represent anti-COVID-19 treatments. Elucidating the metabolic and pharmacokinetic characteristics of AvDs may help pharmacologists to identify new formulations with high bioavailability and efficacy and help physicians to better treat virus-related diseases, including COVID-19.

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Synthesis and Biological Evaluation of NH2-Sulfonyl Oseltamivir Analogues as Influenza Neuraminidase Inhibitors

Cited by 6 publications

References 30 publications

The Inhibitory Activities and Antiviral Mechanism of Medicinal Plant Ingredient Quercetin Against Grouper Iridovirus Infection

The Inhibitory Activities and Antiviral Mechanism of Medicinal Plant Ingredient Quercetin Against Grouper Iridovirus Infection

Triflamides and Triflimides: Synthesis and Applications

Antiviral Drug Delivery System for Enhanced Bioactivity, Better Metabolism and Pharmacokinetic Characteristics

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