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The 1,2,3‐Triazole Ring as a Peptido‐ and Olefinomimetic Element: Discovery of Click Vanilloids and Cannabinoids
Author(s) -
Appendino Giovanni,
Bacchiega Sara,
Minassi Alberto,
Cascio Maria Grazia,
De Petrocellis Luciano,
Di Marzo Vincenzo
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703590
Subject(s) - amide , chemistry , triazole , ring (chemistry) , click chemistry , alkene , stereochemistry , cannabinoid , combinatorial chemistry , receptor , biochemistry , organic chemistry , catalysis
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.