A series of chiral 2,3-dichlorophenoxy and 1-naphthyloxy alkylamines were synthesized, and their binding affinities towards 5-HT(1D) and h5-HT(1B) receptors were evaluated. In the naphthyloxy series, the (R)-prolinol derivative was the most selective 5-HT(1D) ligand, while (S)-N-methyl-2-(1-naphthyloxy)propan-1-amine showed the highest selectivity for h5-HT(1B). Both compounds performed as 5-HT(1D) agonists in the isolated guinea pig assay and showed higher analgesic activity than both sumatriptan and the achiral analogue 20 b in the mouse hot-plate test. Neither ligand displayed any affinity for nicotinic ACh receptors present in mouse brain membranes, thus indicating that their analgesic activity does not arise through interaction with these receptors.

Chiral aryloxyalkylamines: Selective 5-HT(1B/1D) activation and analgesic activity / Carocci A; Lentini G; Catalano A; Cavalluzzi MM; Bruno C; Muraglia M; Colabufo NA; Galeotti N; Corbo F; Matucci R; Ghelardini C; Franchini C.. - In: CHEMMEDCHEM. - ISSN 1860-7179. - STAMPA. - 5:(2010), pp. 696-704. [10.1002/cmdc.200900530]

Chiral aryloxyalkylamines: Selective 5-HT(1B/1D) activation and analgesic activity

GALEOTTI, NICOLETTA;MATUCCI, ROSANNA;GHELARDINI, CARLA;
2010

Abstract

A series of chiral 2,3-dichlorophenoxy and 1-naphthyloxy alkylamines were synthesized, and their binding affinities towards 5-HT(1D) and h5-HT(1B) receptors were evaluated. In the naphthyloxy series, the (R)-prolinol derivative was the most selective 5-HT(1D) ligand, while (S)-N-methyl-2-(1-naphthyloxy)propan-1-amine showed the highest selectivity for h5-HT(1B). Both compounds performed as 5-HT(1D) agonists in the isolated guinea pig assay and showed higher analgesic activity than both sumatriptan and the achiral analogue 20 b in the mouse hot-plate test. Neither ligand displayed any affinity for nicotinic ACh receptors present in mouse brain membranes, thus indicating that their analgesic activity does not arise through interaction with these receptors.
2010
5
696
704
Carocci A; Lentini G; Catalano A; Cavalluzzi MM; Bruno C; Muraglia M; Colabufo NA; Galeotti N; Corbo F; Matucci R; Ghelardini C; Franchini C.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/386772
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