Müller, Klaus and Prinz, Helge and Gawlik, Ingo and Ziereis, Klaus and Huang, Hsu-Shan (1997) Simple analogues of anthralin: Unusual specificity of structure and antiproliferative activity. JOURNAL OF MEDICINAL CHEMISTRY, 40 (23). pp. 3773-3780. ISSN 0022-2623, 1520-4804
Full text not available from this repository.Abstract
Fifty-nine simple analogues of the antipsoriatic agent, anthralin, have been prepared by modifying the positions of the 1,8-hydroxyl groups, replacement of the hydroxyl groups, substitution at the oxygen functions, introduction of additional functional groups into various positions of the anthracenone nucleus, or removal of particular structural elements. The compounds were evaluated for their antiproliferative action against human keratinocytes and inhibition of the generation of leukotriene B-4 in polymorphonuclear leukocytes, which may be useful to resolve the proliferative and inflammatory aspects of psoriasis, respectively. Even though many anthracenones were more potent inhibitors of leukotriene biosynthesis than anthralin, none of the compounds was substantially more effective as this drug in suppressing keratinocyte cell growth. There is an absolute requirement for two hydroxyl groups peri to a hydrogen bond acceptor such as a keto or an imino group for high potency. Ln addition to further delineating the nature of the pharmacophore for this class of compounds, also naphthalenedione with a peri hydroxyl group was identified as a pharmacophore with antiproliferative activity against keratinocyte growth.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MODULATED REDOX PROPERTIES; TOPICAL ANTIINFLAMMATORY ACTIVITY; CULTURED HUMAN KERATINOCYTES; ANTIPSORIATIC ANTHRONES; 5-LIPOXYGENASE INHIBITORS; DITHRANOL; DERIVATIVES; ANTHRACENONES; PSORIASIS; 1,8-DIHYDROXY-9(10H)-ANTHRACENONES |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Mar 2023 08:59 |
| Last Modified: | 02 Mar 2023 08:59 |
| URI: | https://pred.uni-regensburg.de/id/eprint/50415 |
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