Document Detail


Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid analogues.
MedLine Citation:
PMID:  3599023     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of eicosatetraenes (2-24) were designed, synthesized, and evaluated in vitro for inhibitory activity against 5-lipoxygenase (20000g supernatant from homogenized rat basophilic leukemia cells). All compounds were found to be active with the potencies (IC50's) ranging from 0.19 to 97 microM. Compounds containing the hydroxamic acid functionality (10-12) exhibited the best activity (IC50 = 0.19-2.8 microM). The most potent inhibitor was 5-[(hydroxyamino)carbonyl]methyl]-6,8,11,14-eicosatetraenoic acid (11), which was 10 times more active than the C-1 hydroxamates of arachidonic acid or 5-HETE. Cyclization of the linear eicosanoids 2 and 14 in the C-1 to C-5 region produced compounds (21 and 24, respectively) with several-fold greater potency.
Authors:
F A Kerdesky; S P Schmidt; J H Holms; R D Dyer; G W Carter; D W Brooks
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  30     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1987 Jul 
Date Detail:
Created Date:  1987-08-07     Completed Date:  1987-08-07     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  1177-86     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Animals
Arachidonate 5-Lipoxygenase / antagonists & inhibitors*
Arachidonate Lipoxygenases / antagonists & inhibitors*
Arachidonic Acids / chemical synthesis*,  pharmacology
Leukotrienes*
Rats
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Arachidonic Acids; 0/Leukotrienes; 74581-83-2/arachidonic acid 5-hydroperoxide; EC 1.13.11.-/Arachidonate Lipoxygenases; EC 1.13.11.34/Arachidonate 5-Lipoxygenase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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