Stereoselective synthesis, natural occurrence and CB(2) receptor binding affinities of alkylamides from herbal medicines such as Echinacea sp

A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which...

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Veröffentlicht in:	Organic & biomolecular chemistry 2007-01, Vol.5 (1), p.169-174
Hauptverfasser:	Matovic, N, Matthias, A, Gertsch, Jürg, Raduner, Stefan, Bone, K M, Lehmann, R P, Devoss, J J
Format:	Artikel
Sprache:	eng
Schlagworte:	Echinacea - chemistry Molecular Structure Plant Preparations - chemistry Plants, Medicinal - chemistry Polyunsaturated Alkamides - chemical synthesis Polyunsaturated Alkamides - chemistry Polyunsaturated Alkamides - isolation & purification Receptor, Cannabinoid, CB2 - chemistry Receptor, Cannabinoid, CB2 - metabolism Species Specificity Stereoisomerism
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Zusammenfassung:	A divergent synthesis of (2E,4E,8E,10E)- and (2E,4E,8E,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamides from pent-4-yn-1-ol allowed identification of the (2E,4E,8E,10Z)-isomer for the first time in Echinacea species. A short, stereoselective synthesis of the (2E,4E,8E,10Z)-isomer is also described which allowed further biological evaluation of this material, and the demonstration that this isomer does not occur in Spilanthes mauritiana as previously reported.
ISSN:	1477-0520