Relationship between electronic structure and cytotoxic activity of azulenes.
The structure-activity relationship of the cytotoxic activity of azulene and azulene derivatives was discussed, using theoretically calculated results. In order to clearly divide the azulenes into three groups according to their functional groups, the CC50, four different dipole moments (muG, muESP-G, muwand muESP-W) and heats of formation (deltaHf) of the azulenes [1-24] were separately calculated in two states, gas-phase and water, by the conductor-like screening model/parametric method 3 (COSMO/PM3). For the halogenated azulenes and isopropyl azulenes, the cytotoxic activity might follow the three quantitative structure-activity relationship (QSAR) parameters: deltadeltaHf, HOMO energy and muw Whereas, for the other ten compounds [3-5, 7-8, 10, 15-18], the cytotoxic activity might be related to the three QSAR parameters, deltadeltaHf, LUMO energy and muG
Kurihara
Teruo
T
Department of Chemistry, Faculty of Science, Josai University, Sakado, Saitama, Japan. tkuri@josai.ac.jp
Noguchi
Mayumi
M
Noguchi
Takashi
T
Wakabayashi
Hidetsugu
H
Motohashi
Noboru
N
Sakagami
Hiroshi
H
D000970:Antineoplastic Agents / Q000737:chemistry / Q000633:toxicity; D052176:Azulenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008956:Models, Chemical; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D013223:Statistics as Topic; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
D000970:Antineoplastic Agents; D052176:Azulenes; D014867:Water