Abstract
Analogues of 4-Guanidino-Neu5Ac2en (Zanamivir) have been prepared containing carbamate substituents at the 7-hydroxy position. (4S,5R,6R)-5-Acetylamino-6-[1R-[(6-aminohexyl)carbamoyloxy]-2R,3-dihydroxypropyl]-4-guanidino-5,6-dihydro-4H-pyran-2carboxylic acid and (4S,5R,6R)-5-Acetylamino-6-[1R-[heptylcarbamoyloxy]-2R,3-dihydroxypropyl]-4-guanidino-5,6-dihydro4H-pyran2-carboxylic acid were the two analogues possessing activity comparable to Zanamivir, showing potent inhibition of influenza virus sialidases and good antiviral activity in vitro.
MeSH terms
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / pharmacology*
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Crystallography, X-Ray
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / pharmacology*
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Glycerol / chemistry
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Guanidines
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Humans
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Influenza A virus / drug effects
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Influenza A virus / enzymology*
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Influenza B virus / drug effects
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Influenza B virus / enzymology*
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Neuraminidase / antagonists & inhibitors*
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Pyrans
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Sialic Acids / chemical synthesis*
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Sialic Acids / pharmacology*
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Viral Plaque Assay
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Zanamivir
Substances
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Antiviral Agents
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Enzyme Inhibitors
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Guanidines
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Pyrans
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Sialic Acids
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Neuraminidase
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Zanamivir
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Glycerol