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Discovery of (E)-1-amino-4-phenylbut-3-en-2-ol derivatives as novel neuraminidase inhibitors

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  • Discovery of (E)-1-amino-4-phenylbut-3-en-2-ol derivatives as novel neuraminidase inhibitors

    Bioorg Med Chem Lett. 2018 May 4. pii: S0960-894X(18)30392-5. doi: 10.1016/j.bmcl.2018.05.002. [Epub ahead of print]
    Discovery of (E)-1-amino-4-phenylbut-3-en-2-ol derivatives as novel neuraminidase inhibitors.

    Lu C1, Yin Y2, Meng F1, Dun Y1, Pei K1, Wang C1, Xu X1, Wu F1.
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    Neuraminidase has been considered as an important target for designing agents against influenza viruses. In a discovery of anti-influenza agents with epigoitrin as the initial lead compound, a series of 1-amino-2-alkanols were synthesized and biologically evaluated. The in vitro evaluation indicated that (E)-1-amino-4-phenylbut-3-en-2-ol (C1) had better inhibitory activities than 2-amino-1-arylethan-1-ol derivatives. To our surprise, sulfonation of C1 with 4-methoxybenzenesulfonyl chloride afforded more active inhibitor II with up to 6.4 μM IC50 value against neuraminidase. Furthermore, docking of inhibitor II into the active site of NA found that the H atoms in both NH2 and OH groups of inhibitor II were the key factors for potency. Molecular docking research did not explained very well the observed structure-activity relationship (SAR) from amino acid residue level, but also aided the discovery of (E)-1-amino-4-phenylbut-3-en-2-ol derivatives as novel and potent NA inhibitors.


    1-Amino-4-phenylbut-3-en-2-ol derivatives; Influenza; Molecular docking; Neuraminidase; Neuraminidase inhibitor

    PMID: 29748050 DOI: 10.1016/j.bmcl.2018.05.002