The 1,2,3-triazole ring as a peptido- and olefinomimetic element: Discovery of click yanilloids and cannabinoids

Giovanni Appendino; Sara Bacchiega; Alberto Minassi; Maria Grazia Cascio; Luciano De Petrocellis; Vincenzo Di Marzo

doi:10.1002/anie.200703590

The 1,2,3-triazole ring as a peptido- and olefinomimetic element: Discovery of click yanilloids and cannabinoids

Giovanni Appendino^*, Sara Bacchiega, Alberto Minassi, Maria Grazia Cascio, Luciano De Petrocellis, Vincenzo Di Marzo

^*Corresponding author for this work

Medical Sciences

Research output: Contribution to journal › Article › peer-review

62 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	9312-9315
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	48
DOIs	https://doi.org/10.1002/anie.200703590
Publication status	Published - 5 Dec 2007

Keywords

Cannabinoids
Cycloaddition
Drug design
Triazoles
Vanilloids

Access to Document

10.1002/anie.200703590

Cite this

@article{12ed1c1d8d7e4fb2991303909212b16f,

title = "The 1,2,3-triazole ring as a peptido- and olefinomimetic element: Discovery of click yanilloids and cannabinoids",

abstract = "(Chemical Equation Presented) 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.",

keywords = "Cannabinoids, Cycloaddition, Drug design, Triazoles, Vanilloids",

author = "Giovanni Appendino and Sara Bacchiega and Alberto Minassi and Cascio, {Maria Grazia} and {De Petrocellis}, Luciano and {Di Marzo}, Vincenzo",

year = "2007",

month = dec,

day = "5",

doi = "10.1002/anie.200703590",

language = "English",

volume = "46",

pages = "9312--9315",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "WILEY-V C H VERLAG GMBH",

number = "48",

}

TY - JOUR

T1 - The 1,2,3-triazole ring as a peptido- and olefinomimetic element

T2 - Discovery of click yanilloids and cannabinoids

AU - Appendino, Giovanni

AU - Bacchiega, Sara

AU - Minassi, Alberto

AU - Cascio, Maria Grazia

AU - De Petrocellis, Luciano

AU - Di Marzo, Vincenzo

PY - 2007/12/5

Y1 - 2007/12/5

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

KW - Cannabinoids

KW - Cycloaddition

KW - Drug design

KW - Triazoles

KW - Vanilloids

UR - http://www.scopus.com/inward/record.url?scp=37349065872&partnerID=8YFLogxK

U2 - 10.1002/anie.200703590

DO - 10.1002/anie.200703590

M3 - Article

C2 - 17968870

AN - SCOPUS:37349065872

VL - 46

SP - 9312

EP - 9315

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 48

ER -

The 1,2,3-triazole ring as a peptido- and olefinomimetic element: Discovery of click yanilloids and cannabinoids

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this