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  • Title: Relationship between pi-electron distribution and anticancer activity of benzo[a]phenothiazines.
    Author: Motohashi N, Sasaki Y, Wakabayashi Y, Sakagami H, Molnar J, Kurihara T.
    Journal: Anticancer Res; 1992; 12(5):1423-6. PubMed ID: 1444201.
    Abstract:
    In order to study the correlation between the anti-tumor activity of benzo[a]phenothiazines and the electron densities, the Huckel orbital method and modified-neglect-of-diatomic overlap (MNDO) orbital method were used. 9-Methyl-12H-benzo[a]phenothiazine (2), which showed the most potent anticancer activity among benzo[a]phenothiazines, had the highest charge of nitrogen atom (QN), L-region (QL) and M-region (QM) in the molecule. The other derivatives, which showed weaker anticancer activity, had a much reduced value of these charges (QN, QL, QM). The data suggest that stability of pi-electron in 1 benzene ring and 1 naphthalene ring in the benzo[a]phenothiazine skeleton might be responsible for the induction of anticancer activity.
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