Synthesis and cytotoxicity studies of some new amino isoquinolin-5,8-dione and quinolin-5,8-dione derivatives

1098-1109During the search for new cytotoxic drugs, a new series of 7-amino-isoquinoline-5,8-dione and 6-amino-quinoline-5,8-dione derivatives have been synthesised starting from isoquinoline, and 8-hydroxy-quinoline, respectively, through multi-step reactions. The title compounds 7-amino-isoquinoline-5,8-diones have been prepared by treatment of 6-bromo-isoquinoline-5,8-dione with some alkyl/heterocyclic/aromatic amines via nucleophilic tetrahedral mechanism. On the other hand, the corresponding 6-amino-quinoline-5,8-diones have been prepared by treating 7-bromo-quinoline-5,8-dione with some alkyl/heterocyclic/aromatic amines. Rate of reactions depend on the electron availability on the served amino-compounds (i.e. alkyl/heterocyclic/aromatic amines) during their reactions with the corresponding isoquinoline and quinoline quinones. All synthesised compounds have been purified using a series of chromatographic techniques, and their structures have been characterized by NMR spectroscopy and high resolution EI mass spectrometry. The newly synthesised compounds have been evaluated for cytotoxicity using brine shrimps, demonstrating potent cytotoxic activity (95-100%)