Synthesis of toddacoumaquinone, a coumarin-naphthoquinone dimer, and its antiviral activities

Abstract

Toddacoumaquinone (1), a coumarin-naphthoquinone dimer, was synthesized through Diels-Alder reaction between 8-(1-acetoxy-3-methyl-1,3-butadienyl)-5,7-dimethoxycoumarin (15) and 2-methoxy-1,4-benzoquinone (5). The activities of 1 against several viruses were examined. A weak activity (EC50 = 10 micrograms/ml) was observed against HSV-1 and HSV-2, but no activity was seen against HIV-1.