[Studies on 1,4-naphthoquinones. 23. 2-3-Halogen-2-3-nitrophenyljuglone derivatives, synthesis and cytotoxic...

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.