1,2,3-Triazole Ring as a Peptido- and Olefinomimetic Element: Discovery of Click Vanilloids and Cannabinoids

1,2,3-Triazole Ring as a Peptido- and Olefinomimetic Element: Discovery of Click Vanilloids and Cannabinoids

Fooling nature: The replacement of amide and alkene groups in a biological setting with the 1,2,3‐triazole group led to the discovery of compounds with a unique vanilloid/cannabinoid mixed profile. For example, the natural amides (see picture, above) and their triazole mimics (below) exhibit similar...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (48), p.9312-9315
Hauptverfasser: Appendino, Giovanni, Bacchiega, Sara, Minassi, Alberto, Cascio, Maria Grazia, De Petrocellis, Luciano, Di Marzo, Vincenzo
Format: Artikel
Sprache:eng
Schlagworte:
cannabinoids
Cannabinoids - chemistry
Capsaicin - analogs & derivatives
Capsaicin - chemistry
cycloaddition
drug design
Receptor, Cannabinoid, CB1 - antagonists & inhibitors
triazoles
Triazoles - chemistry
TRPV Cation Channels - agonists
TRPV Cation Channels - antagonists & inhibitors
vanilloids
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Zusammenfassung:Fooling nature: The replacement of amide and alkene groups in a biological setting with the 1,2,3‐triazole group led to the discovery of compounds with a unique vanilloid/cannabinoid mixed profile. For example, the natural amides (see picture, above) and their triazole mimics (below) exhibit similar agonistic (X=H) or antagonistic (X=I) activity towards the TRPV1 receptor; however, only the triazole derivatives also show cannabinomimetic activity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200703590