Synthesis of three potential inhibitors of leukotriene biosynthesis.

  title={Synthesis of three potential inhibitors of leukotriene biosynthesis.},
  author={Juerg R. Pfister and Devangachinta Murthy},
  journal={Journal of medicinal chemistry},
  volume={26 8},
The syntheses of 7,7-dimethyl- (1), 10,10-dimethyl- (2), and 5,6-benzoarachidonic acid (3), potential substrate analogue inhibitors of leukotriene biosynthesis, are described. Two of these compounds (1 and 2) apparently stimulated, while 3 inhibited, the activity of lipoxygenase from intact human polymorphonuclear leukocytes in vitro when stimulated with Ca2+ and calcium ionophore A23187 in the presence of BSA and arachidonic acid. 
20 Citations
Inhibition of leukotriene and thromboxane biosynthesis by a 9-(4-chlorophenyl) analogue of arachidonic acid.
The synthesis of 9-(4-chlorophenyl)-7,7-dimethyl-5(Z), 8-nonadienoic acid (7) and its methyl ester 6, and their effects on arachidonic acid metabolism in vitro are described. The IC50 values of 19.6Expand
Synthesis and biological properties of hydroxythioether fatty acids related to leukotrienes: Antagonists and agonists of slow-reacting substance of anaphylaxis (SRS-A)
Abstract A series of 6-hydroxy-7-thioether and 6-thioether-7-hydroxy derivatives of commercially available petroselinic acid and 5-hydroxy-6-thioether derivatives of fatty acids containing anExpand
Leukotriene Biosynthesis Inhibitors
  • J. Cashman
  • Chemistry, Medicine
  • Pharmaceutical Research
  • 2004
The design and current development of leukotriene biosynthesis inhibitors as potential antiinflammatory agents are described and the potential of product inhibitors and mechanism based inactivators of 5-lipoxygenase is discussed. Expand
Synthesis and 5-lipoxygenase inhibitory activity of 7,7-dimethyleicosa-5Z, 8Z-dienoic acid
Abstract Synthesis of 7,7-dimethyleicosa-5Z,8Z-dienoic acid and its inhibitory activity against 5-lipoxygenase is described.
Leukotriene antagonists and inhibitors of leukotriene biosynthesis as potential therapeutic agents.
  • J. Salmon, L. G. Garland
  • Chemistry, Medicine
  • Progress in drug research. Fortschritte der Arzneimittelforschung. Progres des recherches pharmaceutiques
  • 1991
Compounds which limit the effect of these mediators have therapeutic potential are proposed. Expand
1,1-Disubstituted-2,5-cyclohexadines: selective inhibitors of 5-lipoxygenase
Abstract 1,1-Disubstituted-2,5-Cyclohexadienes, modeled after arachidonic acid and 15-HETE, selectively inhibit 5-Lipoxygenase.
Synthesis of methyl (1R,2S)-2-[(1'Z,4'Z,7'Z)-hexadeca-1',4',7'-trienyl]cyclopropanecarboxylate : a potential inhibitor of the enzyme 5-lipoxygenase
We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylideExpand
Analogs of arachidonic acid methylated at C-7 and C-10 as inhibitors of leukotriene biosynthesis.
These arachidonic acid analogs are all inhibitors of ionophore-induced SRS-A biosynthesis in rat peritoneal cells and failed to exhibit significant activity in an in vivo model designed to detect inhibitors of antigen-induced, leukotriene-mediated bronchoconstriction in sensitized guinea pigs. Expand
Synthesis and biological evaluation of new arachidonic acid analogs
Abstract New arachidonic acid analogs selectively modified at the C10 position have been prepared. Several of them are potent and selective leukotriene biosynthesis inhibitors and preliminaryExpand
1,4-Dihydronaphthoquinones as water-soluble inhibitors of 5-lipoxygenase.
The acetate derivatives of 1,4-dihydronaphthoquinones showed significant inhibition of 5-lipoxygenase. Among them, 1-acetyl-2-n-butyl-4-methoxy-naphthalene and 1-acetyl-2, 3-diethyl- 4-Expand