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.

我们在这里报告了一系列带有萘部分的 1 H -indole-2,3-diones ( 2a - f ) 的合成、结构表征和体外抗病毒作用的评估。所有针对不同单纯疱疹病毒 (HSV) 的 1-(naphthalen-2-ylmethyl)-1 H -indole-2,3-diones ( 2c-f ) 被发现在低微摩尔水平下有效 (EC ₅₀ =2.3– 20.0 µM）。用化合物 2d 进行分子动力学和对接模拟，化合物2d表现出最强的抗 HSV 活性，并计算了对 HSV-1 表面糖蛋白 B (gB) 和 D (gD) 的结合亲和力。此外，5-bromo-1-(naphthalen-1-ylmethyl)-1H -indole-2,3-dione ( 2b ) 和 1-(naphthalen-2-ylmethyl)-1 H -indole-2,3-dione ( 2c ) 表现出无毒的抗病毒作用 (EC ₅₀ =6.8–12.0 µM)水疱性口炎病毒 (VSV) 和呼吸道合胞病毒 (RSV)。为了检查萘环的作用，还评估了1-甲基或 1-乙基取代化合物 ( 2g-i ) 的体外抗病毒活性，但这些衍生物对所测试的任何病毒均无抗病毒活性。