1,4-Naphthoquinones. XXIII: 2/3-Halogeno-2/3-nitrophenyl-juglone derivatives, synthesis and cytotoxic properties

Article abstract of DOI:10.1002/ardp.19943271005

Radical arylation of 1,4-naphthoquinones is possible by oxidative decarboxylation of 2- and 4-nitrobenzoic acid. With 2- and 3-halogenojuglone derivatives the 4-nitrophenyl compounds 10-13 are prepared in good, the 2-nitrophenyl analogues 14-17 only in poor yields. - All compounds are inactive against the virus types HSV and HIV and their marked cytotoxicity in part depends on the substitution pattern. The 3-aryl and o-nitro derivatives are more active than their 2-aryl and p-nitro analogues and the influence of the chloro or bromo substitution is only remarkable in the case of 12/13.