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Design, synthesis, and structural analysis of inhibitors of influenza neuraminidase containing a 2,3-disubstituted tetrahydrofuran-5-carboxylic acid core.

Wang GT, Wang S, Gentles R, Sowin T, Maring CJ, Kempf DJ, Kati WM, Stoll V, Stewart KD, Laver G
Bioorg Med Chem Lett 15 125-8 (2005)
Cited: 11 times
EuropePMC logo PMID: 15582424

Abstract

(+/-)-(2R,3R,5R)-[2-(1'-S-acetamido-3'-methyl)butyl-3-methoxycarbonyl]tetrahydrofuran-5-carboxylic acid (9) and (+/-)-(2R,3R,5R)-[2-(1'-S-acetamido-3'-methyl)butyl-3-(4'-imidazolyl)]tetrahydrofuran 5-carboxylic acid (14) were synthesized as inhibitors of influenza neuraminidase (NA). Both compounds 9 and 14 inhibit influenza NA A with an IC(50) of about 0.5 microM and NA B with an IC(50) of 1.0 microM.

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  2. Combining crystallographic information and an aspherical-atom data bank in the evaluation of the electrostatic interaction energy in an enzyme-substrate complex: influenza neuraminidase inhibition. Dominiak PM, Volkov A, Dominiak AP, Jarzembska KN, Coppens P. Acta Crystallogr. D Biol. Crystallogr. 65 485-499 (2009)
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Reviews citing this publication (3)

  1. Antiviral agents active against influenza A viruses. De Clercq E. Nat Rev Drug Discov 5 1015-1025 (2006)
  2. Anti-influenza virus agents: synthesis and mode of action. Lagoja IM, De Clercq E. Med Res Rev 28 1-38 (2008)
  3. A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues. Risseeuw M, Overhand M, Fleet GW, Simone MI. Amino Acids 45 613-689 (2013)

Articles citing this publication (4)

  1. Aureonitol, a Fungi-Derived Tetrahydrofuran, Inhibits Influenza Replication by Targeting Its Surface Glycoprotein Hemagglutinin. Sacramento CQ, Marttorelli A, Fintelman-Rodrigues N, de Freitas CS, de Melo GR, Rocha ME, Kaiser CR, Rodrigues KF, da Costa GL, Alves CM, Santos-Filho O, Barbosa JP, Souza TM. PLoS ONE 10 e0139236 (2015)
  2. Combining docking, scoring and molecular field analyses to probe influenza neuraminidase-ligand interactions. Abu Hammad AM, Afifi FU, Taha MO. J. Mol. Graph. Model. 26 443-456 (2007)
  3. Structure-guided design of a novel class of benzyl-sulfonate inhibitors for influenza virus neuraminidase. Platis D, Smith BJ, Huyton T, Labrou NE. Biochem. J. 399 215-223 (2006)
  4. Molecular docking, synthesis, and biological evaluation of naphthoquinone as potential novel scaffold for H5N1 neuraminidase inhibition. Sharma G, Vasanth Kumar S, Wahab HA. J. Biomol. Struct. Dyn. 36 233-242 (2018)


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