Document Detail

9,11-Epoxy-9-homo-14-oxaprosta-5-enoic acid derivatives. Novel inhibitors of fatty acid cyclooxygenase.
MedLine Citation:
PMID:  3097316     Owner:  NLM     Status:  MEDLINE    
A novel bicyclic prostaglandin analogue, [1R-[l alpha,2 beta (5Z),3 beta,4 alpha]]-7-[3-[(hexyloxy)methyl]- 7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1), and cogeners were found to be potent inhibitors of fatty acid cyclooxygenase. Compound 1 was the only stereoisomer out of eight possible structures that was active. Ether 1 was 20 times more potent than indomethacin (IND) in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound 1 was also more potent than IND in several in vivo assays, AA-induced sudden death in the conscious mouse (2 times) and AA-induced bronchoconstriction in the anesthetized guinea pig (16-45 times).
S E Hall; W C Han; M F Haslanger; D N Harris; M L Ogletree
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  29     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1986 Nov 
Date Detail:
Created Date:  1986-12-24     Completed Date:  1986-12-24     Revised Date:  2004-11-17    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  2335-47     Citation Subset:  IM    
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MeSH Terms
Arachidonic Acid
Arachidonic Acids / pharmacology
Cyclooxygenase Inhibitors*
Indomethacin / pharmacology
Molecular Conformation
Platelet Aggregation / drug effects
Prostaglandins, Synthetic / chemical synthesis*,  pharmacology
Structure-Activity Relationship
Reg. No./Substance:
0/Arachidonic Acids; 0/Cyclooxygenase Inhibitors; 0/Prostaglandins, Synthetic; 506-32-1/Arachidonic Acid; 53-86-1/Indomethacin

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

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