title: Relationship between electronic structure and cytotoxic activity of azulenequinones and trihaloacetylazulenes.
abstract: 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 (DeltaH(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 DeltaDeltaH(f) HOMO energy and mu(ESP-w). The cytotoxic activity of trihaloacetylazulenes was correlated to DeltaDeltaH(f) LUMO energy and mu(ESP-W). QSAR may be applicable to predict the cytotoxicity of azulenequinones and trihaloacetylazulenes.
authors.affiliation: Department of Chemistry, Faculty of Science, Josai University, Sakado, Saitama, Japan. tkuri@josai.ac.jp
authors.forename: Teruo
authors.initials: T
authors.lastname: Kurihara
authors.forename: Rie
authors.initials: R
authors.lastname: Satoh
authors.forename: Takashi
authors.initials: T
authors.lastname: Miyagawa
authors.forename: Hidetsugu
authors.initials: H
authors.lastname: Wakabayashi
authors.forename: Noboru
authors.initials: N
authors.lastname: Motohashi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
mesh_terms: D000107:Acetylation; D052176:Azulenes / Q000737:chemistry* / Q000633:toxicity*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003198:Computer Simulation; D004583:Electrons; D054879:Halogenation; D006801:Humans; D021281:Quantitative Structure-Activity Relationship; D011809:Quinones / Q000737:chemistry* / Q000633:toxicity*
chemical_list: D052176:Azulenes; D011809:Quinones