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Pol J Pharmacol. 1999 Sep-Oct;51(5):415-21.

Effect of the amide fragment on 5-HT1A receptor activity of some analogs of MP 3022.

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Department of Medicinal Chemistry, Institute of Pharmacology, Polish Academy of Sciences, Kraków.


A new set (3-11) of analogs of MP 3022 (1) containing the amide bond inserted into the intermediate chain linking the terminal heteroaromatic and 1-(2-methoxyphenyl)piperazine moieties were prepared and their 5-HT1A and 5-HT2A receptor affinities were determined. Only compounds with trimethylene chain between amide and arylpiperazine fragments (5a, 5b, 7a, 7b and 11) showed satisfactory affinity for 5-HT1A receptor (Ki = 42-87 nM) and high 5-HT2A/5-HT1A selectivity. The new 5-HT1A receptor ligands were investigated in vivo to determine their 5-HT1A agonistic or antagonistic properties. Compounds 7a and 7b with terminal indazole fragment as well as 11 with phenyl substituent behaved like weak 5-HT1A receptor antagonists. The structure-affinity relationship studies in this series of compounds revealed that the amide group along with the terminal aromatic fragments contributed to interaction with 5-HT1A receptor sites, whereas in vivo results indicated that introduction of the amide group into presented arylpiperazine structures was not a profitable modification for their 5-HT1A functional activity.

[Indexed for MEDLINE]

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