- 1,4-THIAZANES AS CONFORMATIONALLY-RESTRICTED ANALOGS OF THE PEPTIDO-LEUKOTRIENES
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A new class of leukotriene antagonists is proposed which represent rigidified approximations of the solution conformation of the peptido-leukotrienes.A representative member of this class has been synthesized and shown to elicit response in the guinea pig ileum assay.
- Ennis, Michael D.,Baze, Mark E.
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- FORMATION AND STRUCTURE DETERMINATION OF 5,6-EPOXY-8,11,14-Z-EICOSATRIENOIC ACID AND 5-OXO-8,11,14-Z-EICOSATRIENOIC ACID
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The formation of 5,6-epoxy-8,11,14-Z-eicosatrienoic acid and 5-oxo-8,11,14-Z-eicosatrienoic acid as by-products in the synthesis of 5-hydroxy-6-E-8,11,14-Z-eicosatetraenoic acid is described.
- Spur, Bernd,Crea, Attilio,Peters, Wilfried
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- LIPID COMPOUNDS AND COMPOSITIONS AND THEIR OPTHALMIC USE
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The invention relates to lipid compounds of formula (I) and their pharmaceutically acceptable salts for the prevention and/or treatment of ophthalmic disorders such as retinal degenerative disorders and ocular inflammatory diseases: (I) (wherein R1 is either a C9 to C22 alkyl group, or a C9 to C22 alkenyl group having from 1 to 6 double bonds; R2 is selected from the group consisting of a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, an alkylthio group, a carboxy group, an acyl group, an amino group, and an alkylamino group; R3 is a hydrogen atom, or a group R2; R4 is a carboxylic acid or a derivative thereof; and X is methylene (-CH2-), or an oxygen or sulfur atom).
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- Epoxidation of polyunsaturated fatty acid double bonds by dioxirane reagent: Regioselectivity and lipid supramolecular organization
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The use of dimethyldioxirane (DMD) as the epoxidizing agent for polyunsaturated fatty acids was investigated. With fatty acid methyl esters, this is a convenient method for avoiding acidic conditions, using different solvents, and simplifying the isolation procedures, with less contamination due to by-products. The reagent was also tested with free fatty acids in water. In this case, the supramolecular organization of fatty acids influenced the reaction outcome, and the epoxidation showed interesting regioselective features. The C=C bonds closest to the aqueous-micelle interface is the most favored for the interaction with dimethyldioxirane. The preferential epoxidation of linoleic acid (=(9Z,12Z)-octadeca-9,12-dienoic acid) to the 9,10-monoepoxy derivative was achieved, with a high yield and 65% regioselectivity. In case of arachidonic acid (=(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-tetraenoic acid) micelles, the regioselective outcome with formation of the four possible monoepoxy isomers was studied under different conditions. It resulted to be a convenient synthesis of 'cis-5,6-epoxyeicosatrienoic acid' (=3-[(2Z,5Z,8Z)-tetradeca-2,5,8- trienyl]oxiran-2-butanoic acid), whereas in reverse micelles, epoxidation mostly gave 'cis-14,15-epoxyeicosatrienoic acid (= (5Z,8Z,11Z)-13-(3-pentyloxiran-2- yl)trideca-5,8,11-trienoic acid).
- Grabovskiy, Stanislav A.,Kabal'nova, Natalia N.,Chatgilialoglu, Chryssostomos,Ferreri, Carla
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p. 2243 - 2253
(2007/10/03)
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- Use of cis-Epoxyeicosantrienoic acids and inhibitors of soluble epoxide hydrolase to reduce pulmonary infiltration by neutrophils
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It has now been discovered that inhibitors of soluble epoxide hydrolase (“sEH”) are useful in reducing the severity of or inhibiting the progression of obstructive pulmonary diseases, restrictive airway diseases, and asthma. Administering a cis-epoxyeicosantrienoic acid (“EET”) in addition to the inhibitor is at least additive, and may be synergistic, in reducing or inhibiting these conditions and diseases, as measured by reduced numbers of neutrophils present in the lung. The inhibitor of sEH may be a nucleic acid, such as a small interfering RNA.
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Page/Page column 12
(2008/06/13)
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- Synthesis of polyconjugated fatty acids
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The present invention relates to fatty acids. In particular, the present invention provides polyconjugated fatty acids, and methods of their synthesis and their use.
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- Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450
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Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs).Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis.Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.
- Falck, J. R.,Manna, S.,Jacobson, Harry R.,Estabrook, R. W.,Chacos, N.,Capdevila, Jorge
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p. 3334 - 3336
(2007/10/02)
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