1: Bioorg Med Chem Lett  2002 Apr 22;12(8):1149-52 

Synthesis and pharmacological evaluation of 6-piperidino- and
6-piperazinoalkyl-2(3H)-benzothiazolones as mixed sigma/5-HT(1A) ligands.

Mouithys-Mickalad A, Poupaert JH, Spampinato S, Lesieur D.

Institut de Chimie Pharmaceutique Albert Lespagnol, Universite de Lille 2, 3,
rue du Professeur Laguesse, F-59006, Lille, France. amouithys@ulg.ac.be

In an effort to produce new pharmacological probes with mixed sigma/5-HT(1A)
affinity, we have synthesized a series of 12 original 6-piperidino- or
piperazino-alkyl-2(3H)-benzothiazolones and their receptor binding profile
(sigma, 5-HT(1A), 5-HT(2A), 5-HT(3), D(2), H(1), and M(1)) was determined. The
best mixed sigma/5-HT(1A) affinity profile was found within the piperidine
series with 4-benzyl substitution associated to linker methylene chain n=2 (K(i)
5 and 4nM, respectively). Moreover, a highly selective sigma2 ligand was
obtained with a 3,4-dichlorobenzyl substitution associated to n=4 (K(i) 2nM,
selectivity ratio sigma1/sigma2=70).

PMID: 11934576 [PubMed - indexed for MEDLINE]