title: Relationship between biological activity and dipole moment in benzo[a]phenothiazines.
abstract: Relationship between the biological activity and two different dipole moments were investigated in 9 benzo[a]phenothiazines [1-8] by calculating the dipole moment with the PM3 method. 12H-Benzo[a]phenothiazine [1], 9-methyl-12H-benzo[a]phenothiazine [2], 10-methyl-12H-benzo[a]phenothiazine[3] and 11-methyl-12H-benzo[a]phenothiazine [4] induced monocytic differentiation of human myelogenous leukemic cell lines and displayed antitumor activity. These active compounds showed a significantly smaller value of calculated ground-state dipole moment (mu g) and larger value of first excited-state dipole moment (mu e). The mu e/mu g ratio of four active compounds [1-4] ranged from 3.25 to 4.38, whereas that of three inactive compounds [5,6,7] ranged from 1.77 to 2.72. These two different dipole moments might be useful parameters for estimation of the biological activity of benzo[a]phenothiazines [1-8].
authors.affiliation: Department of Medicinal Chemistry, Meiji College of Pharmacy, Tokyo, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Motohashi
authors.forename: T
authors.initials: T
authors.lastname: Kurihara
authors.forename: W
authors.initials: W
authors.lastname: Yamanaka
authors.forename: K
authors.initials: K
authors.lastname: Satoh
authors.forename: H
authors.initials: H
authors.lastname: Sakagami
authors.forename: J
authors.initials: J
authors.lastname: Molnár
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry*; D002454:Cell Differentiation / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D051379:Mice; D010640:Phenothiazines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D010640:Phenothiazines; C107575:benzophenothiazine