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

Abstract：

: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.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Lu C,Yin Y,Meng F,Dun Y,Pei K,Wang C,Xu X,Wu F

doi

10.1016/j.bmcl.2018.05.002

subject

Has Abstract

pub_date

2018-06-15 00:00:00

pages

2003-2007

issue

11

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(18)30392-5

journal_volume

28

pub_type

杂志文章

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