Abstract
A new series of rigid analogues (1a-g, 2a-g) of the previously reported analgesic 3-cinnamyl-8-propionyl-3,8-diazabicyclo[3.2.1]octane (I) and its reverted isomer 3-propionyl-8-cinnamyl (II) were synthesized, in which the cinnamyl substituent is incorporated in benzocondensed bicyclic systems. Binding assays for the affinity towards μ receptors indicated that, while in the reverted series 2 the β-naphthylmethyl (2d) and the benzocycloheptenylmethyl derivative (2g) favorably compared with II, all compounds 1 displayed a μ-affinity lower than that of the parent I. Modeling studies suggest that the flexibility of the cinnamyl side chain plays an important role for activity.
Original language | English |
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Pages (from-to) | 667-674 |
Number of pages | 8 |
Journal | Farmaco |
Volume | 53 |
Issue number | 10-11 |
DOIs | |
Publication status | Published - Nov 1998 |
Keywords
- Analgesic activity
- Diazabicyclooctanes
- Opioid receptors
ASJC Scopus subject areas
- Drug Discovery
- Pharmaceutical Science