Design, Synthesis and Biological Evaluation of 2-[4-(Aryl substituted)piperazin-1-yl]acetamido-5-chlorobenzophenone Derivatives

Abstract

Substituted aryl piperazine and its derivatives have attracted great attention due to its diversity of pharmacological activities and its application in heterocyclic synthesis and medicines. It exerts its action on the CNS as it shows its strong affinity towards serotonin and dopamine receptors. The target compounds were synthesized by first reacting p-chloroaniline with chloroacetylchloride to obtain 2-chloro-N-(4-chlorophenyl)acetamide (1), the synthesized compound 1 was further treated with benzoyl chloride in the presence of aluminium chloride to get N-(2-benzoyl-4-chlorophenyl)-2-chloracetamide (2) and then treated with appropriate phenyl piperazine in DMF in the presence of potassium carbonate. The structures were confirmed on the basis of their TLC, IR, ¹H NMR, ¹³C NMR and mass spectra. The physico-chemical parameters were also determined for blood brain barrier penetration. The log P values of the compounds tested showed that compounds have the potential to be CNS active. The compounds were evaluated for the skeletal muscle relaxant activity and it was found that piperazine derivatives possess significant differences between control group and treated group (P < 0.001). Among these derivatives, compound SA4 possesses the highest skeletal muscle relaxant activity.