Design, synthesis, inhibitory activity, and SAR studies of hydrophobic p-aminosalicylic acid derivatives as neuraminidase inhibitors

  • Jie Zhang
  • , Qiang Wang
  • , Hao Fang
  • , Wenfang Xu
  • , Ailin Liu
  • , Guanhua Du

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

A series of hydrophobic p-aminosalicylic acid derivatives containing a lipophilic side chain at C-2 and an amino or guanidine at C-5 were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially available p-aminosalicylic acid (PAS) using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A NA. Within this series, six compounds, 11, 12, 13e, 16e, 17c, and 18e, have the good potency (IC50 = 0.032-0.049 μM), which are compared to Oseltamivir (IC50 = 0.021 μM) and could be used as lead compounds in the future.

Original languageEnglish
Pages (from-to)3839-3847
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number7
DOIs
StatePublished - 1 Apr 2008
Externally publishedYes

Keywords

  • Influenza
  • Neuraminidase inhibitor
  • SAR study
  • p-Aminosalicylic acid derivatives

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