[Studies on 1,4-naphthoquinones. 23. 2-3-Halogen-2-3-nitrophenyljuglone derivatives, synthesis and cytotoxic properties].
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.
Wurm
G
G
Institut für Pharmazie, Freien Universität Berlin.
Gurka
H J
HJ
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006678:HIV / Q000187:drug effects; D006801:Humans; D051379:Mice; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009285:Naphthoquinones
Untersuchungen an 1,4-Naphthochinonen, 23. Mitt.: 2/3-Halogen-2/3-nitrophenyljuglonderivate, Synthese und cytotoxische Eigenschaften.