Anti-influenza drugs and neuraminidase inhibitors

Roberts, Noel A.

doi:10.1007/978-3-0348-8319-1_5

Cited by 15 publications

(6 citation statements)

References 103 publications

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“…The polyvalent liposomal form of this NA-resistant compound was about 10-fold more potent as an inhibitor of X31 virus infection in cell culture than an analogous inhibitor based on the natural sialoside. As an alternative to the design of NA-resistant sialosides, the simultaneous application of -Osialosides and currently available potent NA inhibitors such as oseltamivir carboxylate and zanamivir [83,84] could be used, although this approach has not been tested so far.…”

Section: Synthetic Inhibitors Of Influenza Virus Attachmentmentioning

confidence: 99%

Natural and synthetic sialic acid‐containing inhibitors of influenza virus receptor binding

Matrosovich

Klenk²

2003

Reviews in Medical Virology

138

120

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Influenza viruses attach to susceptible cells via multivalent interactions of their haemagglutinins with sialyloligosaccharide moieties of cellular glycoconjugates. Soluble macromolecules containing sialic acid from animal sera and mucosal fluids can act as decoy receptors and competitively inhibit virus-mediated haemagglutination and infection. Although a role for these natural inhibitors in the innate anti-influenza immunity is still not clear, studies are in progress on the design of synthetic sialic acid-containing inhibitors of receptor binding which could be used as anti-influenza drugs.

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Section: Synthetic Inhibitors Of Influenza Virus Attachmentmentioning

confidence: 99%

Natural and synthetic sialic acid‐containing inhibitors of influenza virus receptor binding

Matrosovich

Klenk²

2003

Reviews in Medical Virology

138

120

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“…Recrystallization was carried out using hexanes/CH 2Cl2 (9:1, v/v): 173 mg, 61% yield; mp 27 107-109°C (lit. 16 3,161.3,155.1,87.2,79.6,63.6,55.7,52.7,52.3,40.6,33.5,28.5,25.8,24.1,12.2,10.9;IR (neat) (()-Methyl 3-(1-Acetylamino-2-ethylbutyl)-4-tert-butoxycarbonylamino-2-hydroxycyclopentanecarboxylate (18). To a solution of 17 (106 mg, 0.3 mmol) in MeOH (10 mL) were added concd HCl (29.7 µL, 0.3 mmol) and PtO 2 (10.2 mg, 0.045 mmol).…”

Section: Experimental Section (()-Cis-4-n-tert-butoxycarbonylamino-2-mentioning

confidence: 98%

“…[3][4][5] When NA cleaves the terminal sialic acid (N-acetyl-D-neuranic acid, 3) from hemagglutinin (HA), new virus particles can be released from the infected cell and spread the infection ( Figure 1). Therefore, inhibition of NA ceases the spread of the infection, trapping viruses inside epithelial cells.…”

Section: Introductionmentioning

confidence: 99%

“…Neuraminidase (NA), the enzyme projecting outward over the viral surface, has emerged as a new therapeutic target for anti-influenza treatment. − When NA cleaves the terminal sialic acid ( N -acetyl- d -neuranic acid, 3 ) from hemagglutinin (HA), new virus particles can be released from the infected cell and spread the infection (Figure ). Therefore, inhibition of NA ceases the spread of the infection, trapping viruses inside epithelial cells.…”

Section: Introductionmentioning

confidence: 99%

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Stereoselective Total Synthesis of Racemic BCX-1812 (RWJ-270201) for the Development of Neuraminidase Inhibitors as Anti-influenza Agents

Mineno

Miller

2003

J. Org. Chem.

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A convergent and versatile racemic total synthesis of the anti-influenza agent BCX-1812 (RWJ-270201) was accomplished on the basis of a sequence of stereoselective reactions. Despite intensive research to develop neuraminidase inhibitors to treat infections due to influenza, currently available agents are still in the need of optimization with respect to selectivity and potency, as well as to minimize adverse effects. Our synthetic approach, introduced in this report, is highly exploitable for further derivatization due to flexibility that will eventually accommodate diversified substituents. In addition, the size of the core ring can be varied depending on the size of the diene used for the preparation of the key cycloadduct 10 using an acylnitroso-based hetero-Diels-Alder reaction. Elaboration of 10 to methyl ester 14 followed by a precedented [3+2] dipolar cycloaddition gave bicyclic isoxazoline 17 in a regio- and stereoselective fashion. Incorporation of the peripheral guanidino group and subsequent deprotection provided the target molecule. The details of the synthesis are described herein.

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“…Furthermore, patients infected with a virus that employs both viral lectins and RDEs may also benefit from treatment with RDE-specific inhibitors, as these can alter the balance between viral lectin and RDE activity which is often crucial for efficient viral replication and spread. Notable examples in this context are the several neuraminidase inhibitors that have been used successfully for the treatment of IAV infections (Kim et al, 1999;Lew et al, 2000;Roberts, 2001;Garman & Laver, 2004;Alymova et al, 2005;von itzstein, 2007;von itzstein & Thomson, 2009;Gamblin & Skehel, 2010;Ikematsu & Kawai, 2011).…”

Section: Targeting Glycan-lectin Interactions In Antiviral Strategiesmentioning

confidence: 99%

Bitter-sweet symphony: glycan–lectin interactions in virus biology

et al. 2014

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Glycans are carbohydrate modifications typically found on proteins or lipids, and can act as ligands for glycan-binding proteins called lectins. Glycans and lectins play crucial roles in the function of cells and organs, and in the immune system of animals and humans. Viral pathogens use glycans and lectins that are encoded by their own or the host genome for their replication and spread. Recent advances in glycobiological research indicate that glycans and lectins mediate key interactions at the virus-host interface, controlling viral spread and/or activation of the immune system. This review reflects on glycan-lectin interactions in the context of viral infection and antiviral immunity. A short introduction illustrates the nature of glycans and lectins, and conveys the basic principles of their interactions. Subsequently, examples are discussed highlighting specific glycan-lectin interactions and how they affect the progress of viral infections, either benefiting the host or the virus. Moreover, glycan and lectin variability and their potential biological consequences are discussed. Finally, the review outlines how recent advances in the glycan-lectin field might be transformed into promising new approaches to antiviral therapy.

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Anti-influenza drugs and neuraminidase inhibitors

Cited by 15 publications

References 103 publications

Natural and synthetic sialic acid‐containing inhibitors of influenza virus receptor binding

Natural and synthetic sialic acid‐containing inhibitors of influenza virus receptor binding

Stereoselective Total Synthesis of Racemic BCX-1812 (RWJ-270201) for the Development of Neuraminidase Inhibitors as Anti-influenza Agents

Bitter-sweet symphony: glycan–lectin interactions in virus biology

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