4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine (7) and its derivatives modified at the carbonyl group of the fluorobenzoyl moiety were prepared and evaluated for affinity at 5-HT2A, 5-HT2C (rat cortex) and 5-HT2B (rat stomach fundus) serotonin receptors. Compound 7 bound the 5-HT2A sites with higher affinity (Ki = 8.2 nM) than the 5-HT2B (Kb = 1 290 nM) and 5-HT2C ones (Ki= 54.2 nM). Modification of the benzoyl carbonyl group decreased the 5-HT2A and 5-HT2C affinities but did not significantly influence 5-HT2B affinity. This suggests that the carbonyl group is the determinant for the interaction with 5-HT2A and 5-HT2C receptor subtypes. Compound 7 was found to be a 5-HT2A receptor antagonist.
4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine and its derivatives: Synthesis and affinity at 5-HT(2A), 5-HT(2B) and 5- HT(2C) serotonin receptors
GESSI, Stefania;SINISCALCHI, Anna;BOREA, Pier Andrea
1999
Abstract
4-(4-Fluorobenzoyl)-1-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]piperidine (7) and its derivatives modified at the carbonyl group of the fluorobenzoyl moiety were prepared and evaluated for affinity at 5-HT2A, 5-HT2C (rat cortex) and 5-HT2B (rat stomach fundus) serotonin receptors. Compound 7 bound the 5-HT2A sites with higher affinity (Ki = 8.2 nM) than the 5-HT2B (Kb = 1 290 nM) and 5-HT2C ones (Ki= 54.2 nM). Modification of the benzoyl carbonyl group decreased the 5-HT2A and 5-HT2C affinities but did not significantly influence 5-HT2B affinity. This suggests that the carbonyl group is the determinant for the interaction with 5-HT2A and 5-HT2C receptor subtypes. Compound 7 was found to be a 5-HT2A receptor antagonist.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
