Relationship between electronic structure and cytotoxic activity of azulenequinones and trihaloacetylazulenes
Kurihara, T.; Satoh, R.; Miyagawa, T.; Wakabayashi, H.; Motohashi, N.; Sakagami, H.
In Vivo 21(5): 715-720
2007
ISSN/ISBN: 0258-851X PMID: 18019403 Document Number: 608624
The relationship between the structure and cytotoxic activity of azulenequinones and trihaloacetylazulenes was investigated based on theoretical calculations. Four different dipole moments (mu(G), mu(ESP-G), mu(W) and mu(ESP-W)) and heats of formation (,Delta H-f) of the azulenequinones [1-27] and trihaloacetylazulenes [28a,b-40a,b] were separately calculated in gas phase and aqueous solution using the conductor-like screening model/parametric method 3 (COSMO/PM3) method. The cytotoxic activity of azulenequinones was well correlated to Delta Delta H-f HOMO energy and mu(ESP-w), The cytotoxic activity of trihaloacetylazulenes was correlated to Delta Delta H-f LUMO energy and mu(ESP-W) QSAR may be applicable to predict the cytotoxicity of azulenequinones and trihaloacetylazulenes.