Tautomerism in 11-Hydroxyaklavinone: A DFT Study
SCIENTIFIC WORLD JOURNAL, 2012 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Publication Date: 2012
- Doi Number: 10.1100/2012/526289
- Journal Name: SCIENTIFIC WORLD JOURNAL
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Open Archive Collection: AVESIS Open Access Collection
- Middle East Technical University Affiliated: Yes
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).