ABSTRACT
New 7-(2-aminoethyl)-7H-benzo[4,5]indolo[2,3-b]quinoxalines (13-20) were synthesized with high yields starting from 3H-benzo[e]indole-1,2-dione. These compounds were screened for the cytotoxicity, anti-viral activity, interferon inducing ability and DNA affinity compared with the corresponding 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxaline derivatives (1-12). It was shown, that compounds 13-20 bind to DNA stronger (lg Ða=6.23-6.87) than compounds 1-12 (lg Ða=5.57-5.89). Anti-viral activity is significantly reduced with annulations of benzene ring in Indoloquinoxaline moiety 13-20.
Subject(s)
Antiviral Agents/pharmacology , DNA/drug effects , Fibroblasts/drug effects , Indoles/pharmacology , Quinoxalines/pharmacology , Vesiculovirus/drug effects , Animals , Antiviral Agents/chemical synthesis , Antiviral Agents/chemistry , Cattle , Indoles/chemical synthesis , Indoles/chemistry , Mice , Microbial Sensitivity Tests , Molecular Structure , Quinoxalines/chemical synthesis , Quinoxalines/chemistry , Stereoisomerism , Structure-Activity RelationshipABSTRACT
New 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields using bromoethylisatin and 6-(2-bromoethyl)-6H-indolo[2,3-b]quinoxaline as intermediates. These compounds were screened for the cytotoxicity, antiviral activity and interferon inducing ability. It was shown, that tested 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines are low toxic potent interferon inducers and antivirals. Morpholine and 4-methyl-piperidine derivatives appeared as the most active antivirals and the least cytotoxic in the investigated series.
