Relationship between pi-electron distribution and anticancer activity of benzo[a]phenothiazines.

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.

• Authors: N Motohashi, Y Sasaki, Y Wakabayashi, H Sakagami, J Molnar, T Kurihara
• Journal: Anticancer research (Anticancer Res) 1992 Sep-Oct Vol. 12 Issue 5 Pg. 1423-6 ISSN: 0250-7005 [Print] Greece
• PMID: 1444201 (Publication Type: Comparative Study, Journal Article)

Chemical References

• Antineoplastic Agents
• Phenothiazines

Topics

• Animals
• Antineoplastic Agents (chemistry, therapeutic use)
• Molecular Structure
• Phenothiazines (chemistry, therapeutic use)
• Structure-Activity Relationship