Antiviral activity and molecular modeling studies on 1H-indole-2,3-diones carrying a naphthalene moiety

•1H-indole-2,3-diones (2a-f) bearing a naphthalene ring were synthesized.•The antiviral effects of 2a-f were evaluated against different DNA and RNA viruses.•2b and 2c exhibited non-toxic antiviral effects at µM levels against VSV and RSV.•2d showed the strongest activity at µM levels against HSVs.•...

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Bibliographic Details
Published in:Journal of molecular structure 2023-06, Vol.1281, p.135100, Article 135100
Main Authors: Soylu-Eter, Özge, Duran, Gizem Nur, Özbil, Mehmet, Göktaş, Füsun, Cihan-Üstündağ, Gökçe, Karalı, Nilgün
Format: Article
Language:English
Subjects:
1H-indole-2,3-dione
Antiviral activity
Herpes simplex viruses
Molecular modeling
Naphthalene
Respiratory syncytial virus
Vesicular stomatitis virus
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Summary:•1H-indole-2,3-diones (2a-f) bearing a naphthalene ring were synthesized.•The antiviral effects of 2a-f were evaluated against different DNA and RNA viruses.•2b and 2c exhibited non-toxic antiviral effects at µM levels against VSV and RSV.•2d showed the strongest activity at µM levels against HSVs.•Modeling study of 2d was performed against HSV-1 surface glycoproteins B and D. We here report the synthesis, structural characterization, and evaluation of the in vitro antiviral effects of a series of 1H-indole-2,3-diones (2a-f) bearing a naphthalene moiety. All 1-(naphthalen-2-ylmethyl)-1H-indole-2,3-diones (2c-f) tested against different herpes simplex viruses (HSVs) were found to be effective at low micromolar levels (EC50=2.3–20.0 µM). Molecular dynamics and docking simulations were performed with compound 2d which exhibited the strongest activity against HSVs and the binding affinities for HSV-1 surface glycoproteins B (gB) and D (gD) were calculated. Moreover, 5-bromo-1-(naphthalen-1-ylmethyl)-1H-indole-2,3-dione (2b) and 1-(naphthalen-2-ylmethyl)-1H-indole-2,3-dione (2c) exhibited nontoxic antiviral effects (EC50=6.8–12.0 µM) against vesicular stomatitis virus (VSV) and respiratory syncytial virus (RSV). To examine the contribution of the naphthalene ring, 1-methyl or 1-ethyl substituted compounds (2g-i) were also evaluated for in vitro antiviral activity, but these derivatives showed no antiviral activity against any of the viruses tested. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2023.135100