Synthesis of transition-state analogues as potential inhibitors of sialidase from Influenza virus.
Sodium 5-acetamido-2,6-anhydro-3,4,5-trideoxy-D-manno-non-2-enonate (2) has been synthesized from N-acetyl-4-deoxy-neuraminic acid methyl ester (4). Sodium 2,6-anhydro-3-deoxy-L-arabino-hept-2-enonate (3), 4-acetamido-2,6-anhydro-3,4-dideoxy-L-arabino-hept-2-enonic acid (18e), and 4-acetamido-2,6-anhydro-3,4-dideoxy-L-ribo-hept-2-enonic acid (18a) have been prepared from L-arabinose. The above compounds were investigated as inhibitors of sialidase from Influenza virus. Only compound 2 showed a significant inhibitory activity (Ki 8 x 10(-2) mM) against the enzyme.
Driguez
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PA
Laboratoire de Chimie Organique, Institut National des Sciences Appliquées, Villeurbanne, France.
Barrere
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B
Quash
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G
Doutheau
A
A
D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*
D001089:Arabinose; D009439:Neuraminidase; D008358:Mannose