Mueller, Klaus and Altmann, Reinhold and Prinz, Helge (2002) 2-arylalkyl-substituted anthracenones as inhibitors of 12-lipoxygenase enzymes. 2. Structure-activity relationships of the linker chain. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 37 (1): PII S0223-. pp. 83-89. ISSN 0223-5234
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A series of 2-arylalkyl-substituted anthracenones were tested as inhibitors of three types of 12-lipoxygenase isoforms in epidermal homogenate of mice, bovine platelets and porcine leukocytes. Their inhibitory activities were compared with those to inhibit the 5-lipoxygenase enzyme in bovine leukocytes. The compounds were synthesised by Marschalk, Wittig or Horner-Emmons reaction at the anthracenedione stage and then reduced to the anthracenones. Structure-activity relationship for the chain linking the anthracenone nucleus and the phenyl ring terminus was investigated. The 2-phenylethyl analogues were among the most potent inhibitors, and 3,4-dimethoxy-substituted 10f was identified as a selective inhibitor of the 12-LO enzymes over 5-LO. Selectivity for 12-LO isoforms was observed with an increase in the overall lipophilicity of the inhibitors. However, none of the linker chains of the 2-substituted anthracenones provided inhibitors that were able to discriminate between the 12-LO isoforms. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MODULATED REDOX PROPERTIES; ANTIPSORIATIC ANTHRONES; ANTIPROLIFERATIVE ACTIVITY; CHROMOSOMAL LOCALIZATION; PLATELET-TYPE; 5-LIPOXYGENASE; KERATINOCYTES; DERIVATIVES; NEUTROPHILS; EXPRESSION; anthracenone; 12(S)-HETE; lipophilicity; 5-lipoxygenase; 12-lipoxygenase |
| Subjects: | 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Medicine > Lehrstuhl für Innere Medizin I |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 16 Nov 2021 06:02 |
| Last Modified: | 16 Nov 2021 06:02 |
| URI: | https://pred.uni-regensburg.de/id/eprint/40735 |
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