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).

• Authors: Lemi Türker
• Journal: TheScientificWorldJournal (ScientificWorldJournal) Vol. 2012 Pg. 526289 ( 2012) ISSN: 1537-744X [Electronic] United States
• PMID: 22623911 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Naphthacenes
• aklavinone
• Daunorubicin

Topics

• Antineoplastic Agents (chemistry)
• Chemical Phenomena
• Daunorubicin (analogs & derivatives, chemistry)
• Isomerism
• Molecular Structure
• Naphthacenes (chemistry)
• Quantum Theory
• Spectrophotometry, Infrared