The reaction of 6,7-dichloro-5,8-quinoxalinedione with aromatic and aliphatic dinucleophiles and molecular modeling study of their intercalation complexes

Abstract

The angular and planar heterocyclic compounds containing nitrogen, sulfur and oxygen were synthesized by reaction of 6,7-dichloro-5,8-quinoxalinedione with aromatic and aliphatic dinucleophiles. Nucleophilic reactivity was somewhat different between 2,3-dichloro-1, 4-naphthoquinone and 6,7-dichloro-5,8-quinolinedione with dinucleophiles. The distribution of electron in heterocycle appeared to contribute to this difference. The intercalation comple of planar heterocyclic compound between GC/GC base pairs showed the optimum intercalation but the intercalation of angular heterocyclic compound was not good, Thus, the planar compound was expected to have antitumor activity.