Synthesis and Screening of Anti-HSV-1 Activity of Thioglucoside Derivatives of Natural Polyhydroxy-1,4-Naphthoquinones

Abstract

Four 1,4-naphthoquinone dithioglucoside derivatives based on natural polyhydroxy-1,4-naphthoquinones were synthesized. These thioglucosides were screened for their antiradical and antiviral activity in vitro. Antiradical activity of tested compounds was determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay. The anti-herpes simplex virus type 1 (anti-HSV-1) activity of thioglucosides was analyzed by the cytopathic effect inhibition assay and mode of antiviral action was determined by the addition of the tested compounds to uninfected cells, to the virus prior to infection, or to herpes-infected cells. Most effective inhibition of HSV-1 replication was observed at pretreatment of virus by the compounds (direct virucidal effect). The dithioglucoside conjugate with the single β-OH group and lipophilic ethyl substituent in naphthoquinone core showed the greatest antiviral activity.

Drug Development for the Management of Corona Viruses: Insights from Natural Antiviral Agents

“…It has been reported to reduce measles virus entry considerably suggesting its interaction with viral particles to reduce infectivity. 146 Some synthetic Bis-Naphthoquinones have also been reported effective against Zika virus 151 and HSV-1 152 suggesting possible use of naphthoquinones as antiviral lead compounds. Optimizing synthetic derivatives of this compound as agents that can block viral entry is a possible consideration for anti-coronavirus and/or SARS-CoV-2 drug development.…”

Design, synthesis, and evaluation of 1,4-naphthoquinone-chromene hybrids as potential anti-K562 and A549 agents

“…4, 5 1,4-Naphthoquinone, a secondary metabolite produced by many plants, animals, algae and fungi, is the most widely used class of naphthoquinone compounds. 6,7 It has received widespread attention due to its extensive pharmacological activities, such as antibacterial, 8 anti-inflammatory, 9 antiviral, 10 and antitumor 11,12 properties. Especially in terms of antitumor effects, psychorubrin, isolated from the aerial parts of Mitracarpus frigidus, displayed promising antitumor effects on HL60, Jurkat and MCF-7 cells.…”

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

“…Naphthoquinones often possess poor solubility which has hampered their practical use. The conjugation of naphthoquinones with non-toxic carbohydrates is one of the most successful ways for improving their solubility [ 15 , 16 , 17 , 18 , 19 ]. Moreover, the conjugation of naphthoquinones with carbohydrates led to novel structures with new types of biological activity [ 20 , 21 ].…”