Synthesis, identification and molecular docking studies of N-functionalized piperidine derivatives linked to 1,2,3-triazole ring

Abstract

New derivatives of piperidine bearing a 1,2,3-triazole ring designed and synthesized smoothly over six steps from N-protected piperidone-4-one. These steps included reduction of the carbonyl group/tosylation of the resulting alcohol providing tosyl derivative in a good yield, followed by nucleophilic substitution and Cu-catalysed azide-alkyne cycloaddition. By removing the protecting group and functionalizing amine group via reductive amination gave the desired design in moderate to very good yields. Molecular modeling studies of these compounds predicted possible binding modes into the active site of dopamine receptor D2.

Graphical Abstract

Keywords:

• DRD2 binding
• ligand docking
• piperidine
• reductive amination
• triazole

Disclosure statement

The authors declare no conflict of interest.

Additional information

Funding

This work was financially supported by the Ministry of Higher Education and Scientific Research – Iraq (MOHESR) (Rafid S. Dawood), and Higher Committee for Education Development in Iraq (HCED) (Sudad A. Dayl).