Abstract
Structural modification of the potent conformationally constrained tricyclic pyrazole CB1 ligand NESS0327 was achieved by replacing: (1) the chlorine substituent on the tricycle with a 3-fluoropropyl chain, and (2) the pyrazole 3-{[(piperidino)amino]carbonyl} substituent with a 4-substituted 1,2,3-triazole group obtained by click chemistry from an alkynyl precursor. Among the resulting compounds, two are particularly promising candidates for [18F]radiolabelling and PET imaging studies of the CB1 receptor, as they displayed K i CB1 = 62.5 nM and 42.5 nM, respectively, in the same range as that displayed by rimonabant.
Original language | English |
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Pages (from-to) | 817-826 |
Number of pages | 10 |
Journal | Synthesis |
Volume | 47 |
Issue number | 6 |
Early online date | 16 Jan 2015 |
DOIs | |
Publication status | Published - Mar 2015 |
Keywords
- cannabinoids
- click chemistry
- fluorine
- PET imaging
- Sonogashira reaction