Pyrazoles with a "click" 4-[N-(4-fluorobutyl)-1,2,3-triazole] substituent in position 3 are nanomolar CB1 receptor ligands

Rita Distinto, Chiara Zanato, Serena Montanari, Maria Grazia Cascio, Paolo Lazzari, Roger Pertwee, Matteo Zanda*

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Replacement of the 3-carbonylaminopiperidine substitutent with a "click" 4-[N-(4-fluorobutyl)-(1,2,3-triazolyl)] group in Rimonabant-type pyrazoles produced a novel class of nanomolar CB1 receptor ligands. Molecule 1d is the most promising lead with a Ki = 23 nM for CB1, which is very close to that displayed by Rimonabant (SR141716), and fairly good CB1/CB2 selectivity (Ki CB2/Ki CB1 = 35.5), thus representing a promising candidate for [18F]radiolabeling and PET Imaging studies of the CB1 receptor.

Original languageEnglish
Pages (from-to)184-191
Number of pages8
JournalJournal of Fluorine Chemistry
Volume167
Early online date21 Jul 2014
DOIs
Publication statusPublished - Nov 2014

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Keywords

  • "Click" chemistry
  • Cannabinoids
  • Fluorine
  • PET imaging
  • Sonogashira reaction

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Environmental Chemistry

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