Synthesis and pharmacological evaluation of novel 4-(4-fluorobenzoyl)piperidine derivatives as mixed 5-HT1A/5-HT2A/D2 receptor ligands

6-Sulfonylbenzothiazolones as potential scaffolds for the design of 5-HT6 ligands

“…A first route (route A) was attempted by introducing 1-amino naphthalene in pyridine to afford derivative 23 with 59% yield, which was placed in dry THF with methyl iodide to afford only the N-methyl benzothiazol-2-one derivative 24, and not the expected N-methylsulfonamide derivative. In the literature, substitution reaction of halogenoalkyl benzothiazolone derivatives with amino reagent was performed in acetone or acetonitrile in the presence of triethylamine [32]. In these conditions no substitution reaction was observed at the free NH benzothiazolone compound.…”

2(3H)-Benzoxazolone and Bioisosters as “Privileged Scaffold” in the Design of Pharmacological Probes

“…In a further effort to improve the profile of this class of structures, a 4fluorophenylpiperidine moiety (as found in ketanserine) was implemented via a two carbon linker to produce additional 5-HT2A antagonism. The most interesting compound in this series OD36 (32), a benzothiazolinone derivative showed noteworthy anti-panic activity in animal models and entered preclinical studies [76][77][78] (Fig. 7).…”

High-Throughput Screening of the ReFRAME Library Identifies Potential Drug Repurposing Candidates for Trypanosoma cruzi

“…Interestingly, we identified two compounds with intriguing primary indications that may target T. cruzi by novel mechanisms. First, serotonin receptor ligands such as 3-[4-[4-(2-Methoxyphenyl) piperazine-1-yl]butyl]-6-[2-[4-(4-fluorobenzoyl)piperidine-1-yl]ethyl]benzothiazole-2(3H)-one [27] have been investigated as agents to treat anxiety and panic disorders. This compound had an EC 50 of 22 nM and a SI of 145, making it an attractive candidate for drug repurposing and animal model testing.…”