- Solid-phase synthesis of anandamide analogues
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The endocannabinoids are amides and esters of arachidonic acid that can mimic the pharmacological properties of Δ9-tetrahydrocannabinol (Δ9-THC). Anandamide, the most prominent of the endocannabinoids, has been implicated in both metabolic/physiological roles of the central nervous system, making it an attractive medicinal target. As such, we report the first solid-phase methodology that expedites access to various anandamide analogues. Our synthesis features a repetitive Cu-mediated coupling reaction between terminal alkynes and propargyl halides or allylic halides.
- Qi, Longwu,Meijler, Michael M.,Lee, Sang-Hyeup,Sun, Chengzao,Janda, Kim D.
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- Synthesis of Arachidonic Acid and Its Acetylenic Precursor
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(5Z,8Z,11Z,14Z)-Eicosatetraenoic (arachidonic) acid and its precursor, 5,8,11,14-eicosatetraynoic acid, were synthesized by the polyacetylene approach using the cross coupling of propargyl iodides and highly reactive organometallic complexes of terminal acetylenic synthons formed in situ. - Key words: arachidonic acid; 5,8,11,14-eicosatetraynoic acid; cross coupling; copper(I) catalysis
- Ivanov, I. V.,Groza, N. V.,Mnasina, E. E.,Myagkova, G. I.
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p. 696 - 699
(2007/10/03)
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- Eicosatetraynoic acid amides and their application in pharmacy
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Compound, characterized in that it corresponds to the formula: in which R is an amino group of structure STR1 in which R1 and R2, which may be identical or different, denote a hydrogen atom or a linear or branches C1 -C8 lower alkyl radical substituted with at least one hydroxyl group, it being possible for this C1 -C8 lower alkyl radical to be interrupted by one or more hetero atoms chosen from oxygen, nitrogen or sulphur, R1 and R2 not simultaneously denoting a hydrogen atom and it being possible for R1 and R2 to form, with the nitrogen atom to which they are attached, a heterocycle containing one or more nitrogen, oxygen or sulphur atoms as an additional hetero atom, it being possible for this heterocycle to be optionally substituted with an alkyl or a hydroxyalkyl, and it also being possible for the amino group to be derived from a sugar, and their salts with inorganic or organic acids. These compounds are used, in particular, in the treatment and prophylaxis of allergic conditions and in the treatment of dermatoses and inflammatory conditions.
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