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
Novel N-(benzoimidazophenyl)dialkylaminoalkylamides and 6-dialkylaminoalkylbenzoimidazo[1,2-c]quinazolines were prepared as potential interferon inducers and antiviral agents. They were screened for the DNA affinity by the ethidium bromide displacement assay. It was shown that the lg K(a) values of the compounds containing tetracyclic benzoimidazo[1,2-c]quinazoline fragment are approximately one order magnitude greater than those of the corresponding acyclic phenylbenzoimidazole derivatives.
