Tautomerism in 11-hydroxyaklavinone: A DFT study

Abstract

The antharquinone-based chromophore of 11-hydroxyaklavinone is present in the structure of an anticancer agent, daunomycin. On the other hand, aklavinone is the parent aglycone of certain anthracycline antibiotics that possess anti-cancer activity too. The structures of aklavinone and its 11-hydroxy derivative have many -OH groups, and two keto groups which may take place in certain tautomeric equilibria. Of these tautomeric forms, presently the one involving the anthraquinone based tautomers of 11-hydroxyaklavinone has been investigated quantum chemically in the framework of the density functional theory at the levels of RB3LYP/6-31G(d) and RB3LYP/6-31G(d,p). Copyright © 2012 Lemi Trker.