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Journal of Enzyme Inhibition and Medicinal Chemistry

Journal of Enzyme Inhibition and Medicinal Chemistry

IF: 5.6
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Synthesis and dual D2 and 5-HT1A receptor binding affinities of 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones.

Published:1 April 2014 DOI: 10.3109/14756366.2013.776556 PMID: 23488743
Nisar Ullah

Abstract

A series of new 5-piperidinyl and 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones have been synthesized and evaluated for dual D2 and 5-HT1A receptor binding affinities. The synthesized ligands are structurally related to bifeprunox, a potential atypical antipsychotic, having potent D2 receptor antagonist and 5-HT1A receptor agonist properties. The Suzuki-Miyaura reaction of cyclic vinyl boronate with appropriate aryl halide yielded arylpiperidine, which was eventually transformed to piperidinyl-1H-benzo[d]imidazol-2(3H)-one. The reductive amination of the latter with appropriate biarylaldehdyes rendered the synthesis of 5-piperidinyl-1H-benzo[d]imidazol-2(3H)-ones. Likewise, the Buchwald-Hartwig coupling reactions of 1-boc-piperazine with appropriate aryl halide and subsequent removal of the boc group rendered arylpiperazine. The reductive amination of the latter with appropriate biarylaldehdyes accomplished the synthesis of 5-piperazinyl-1H-benzo[d]imidazol-2(3H)-ones. The structure-activity relationship studies showed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.

Synthesis

Dichloromethane
4-Methylmorpholine N-oxide
1H-Benzimidazole-5-carboxylic acid
4-Bromo-2-nitroaniline
1H-BENZIMIDAZOLE-5-CARBOXALDEHYDE 97+%

Substances (3)

Related products
Procduct Name CAS Molecular Formula Supplier Price
1-BOC-Piperazine 57260-71-6 C9H18N2O2 834 suppliers $5.00-$12970.00
1-BOC-PIPERAZINE 57260-72-7 C11H20N2O6 154 suppliers Inquiry
7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3H-benzooxazol-2-one 350992-10-8 C24H23N3O2 14 suppliers Inquiry

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