SYNTHESIS OF SOME NOVEL 3,5,6-TRISUBSTITUTED-[1,2,4]TRIAZOLO[3,4-c][1,2,4] TRIAZINESAS DNA PHOTOCLEAVING AGENTS
Keywords:
Pyrazole, Triazole, Triazine, Hypervalent Iodine, DNA photocleavageAbstract
Objective: To develop an easy and non toxic method for synthesis of some novel triazolotriazines via oxidative transformation of triazinylhydrazones using iodobenzene diacetate and to evaluate their DNA photocleavage potential.
Methods: A series nineteen triazin-3-yl moiety linked hydrazones of various aryl and heteroaryl aldehydes has been prepared which on treatment with iodobenzene diacetate in dichloromethane gave novel triazolo[3,4-c]triazine derivatives under mild reaction conditions. DNA photocleavage activity of all these compounds was performed using agarose gel electrophoresis.
Results: Synthesis of some novel triazolotriazines has been successively achieved and structures of compounds were established on the basis of FT-IR, 1H, 13C NMR and mass spectral data. Most of the compounds such as 4m-n, 4p-s, as well as 3b, 3d, 3e, 3h, 3p and 3q exhibited admirable DNA photocleavage potential.
Conclusion: The employed approach to afford triazolo[3,4-c]triazines only because the Dimorth rearrangement occurred under catalytic amount of base and acid etc. The results indicated that both triazolotriazines and triazinylhydrazones exhibited promising DNA photocleavage activity. Moreover, compounds containing phenyl ring with electron-releasing substituent attached to pyrazole nucleus possessed increased DNA photocleavage potential.
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