Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Identifieur interne : 000189 ( Main/Exploration ); précédent : 000188; suivant : 000190Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Auteurs : Yixian Liao [République populaire de Chine] ; Yilu Ye [République populaire de Chine] ; Sumei Li [République populaire de Chine] ; Yilian Zhuang [République populaire de Chine] ; Liye Chen [République populaire de Chine] ; Jianxin Chen [République populaire de Chine] ; Zining Cui [République populaire de Chine] ; Lijian Huo [République populaire de Chine] ; Shuwen Liu [République populaire de Chine] ; Gaopeng Song [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2020.
Abstract
Currently, influenza PAN endonuclease has become an attractive target for development of new drugs to treat influenza infections. Herein we report the discovery of new PAN endonuclease inhibitors derived from a chelating agent dopamine moiety. A series of dopamine amide derivatives and their conformationally constrained 1,2,3,4-tetrahydroisoquinoline-6,7-diol-based analogs were elaborated and assayed against influenza virus A/WSN/33 (H1N1). Most compounds exhibited moderate to excellent antiviral activities, generating a preliminary SARs. Among them, compounds 14 and 19 showed stronger anti-IAV activity compared with the reference Peramivir. Moreover, 14 and 19 demonstrated a concentration-dependent inhibition of PAN endonuclease based on both FRET assay and SPR assay. Docking studies were also performed to elucidate the binding mode of 14 and 19 with the PAN protein and to identify amino acids involved in their mechanism of action, which were well consistent with the biological data. This finding was beneficial to laying the foundation for the rational development of more effective PAN endonuclease inhibitors.
DOI: 10.1016/j.ejmech.2020.112048
PubMed: 31954881
Affiliations:
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<front><div type="abstract" xml:lang="en">Currently, influenza PA<sub>N</sub>
endonuclease has become an attractive target for development of new drugs to treat influenza infections. Herein we report the discovery of new PA<sub>N</sub>
endonuclease inhibitors derived from a chelating agent dopamine moiety. A series of dopamine amide derivatives and their conformationally constrained 1,2,3,4-tetrahydroisoquinoline-6,7-diol-based analogs were elaborated and assayed against influenza virus A/WSN/33 (H1N1). Most compounds exhibited moderate to excellent antiviral activities, generating a preliminary SARs. Among them, compounds 14 and 19 showed stronger anti-IAV activity compared with the reference Peramivir. Moreover, 14 and 19 demonstrated a concentration-dependent inhibition of PA<sub>N</sub>
endonuclease based on both FRET assay and SPR assay. Docking studies were also performed to elucidate the binding mode of 14 and 19 with the PA<sub>N</sub>
protein and to identify amino acids involved in their mechanism of action, which were well consistent with the biological data. This finding was beneficial to laying the foundation for the rational development of more effective PA<sub>N</sub>
endonuclease inhibitors.</div>
</front>
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