A new series of 9-O-3-(1-piperazinyl/morpholinyl/piperidinyl)pentyl-berberines has been efficiently
formulated via coupling 1,5-dibromopentane with berberrubine which was obtained by treating berberine in a vacuum
oven at optimum temperature and pressure. Nucleophilic substitution of a variety of substituted piperazines,
morpholine, carbazole and piperidine furnished analogues 5a-i. Final compounds were evaluated for their in vitro
antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-
sulphonic acid) (ABTS) bioassays. Also, cancer cell inhibitory potential of titled compounds was screened for cervical
cancer, HeLa and CaSki employing SRB assay in terms of cytotoxicity. A minimum inhibitory concentration of
5a-i towards normal cells was studied using Madin-Darby canine kidney (MDCK) cell line. Final compounds with carbazole and
1-(naphthalen-2-yl)piperazine showed excellent free radical scavenging efficacies in DPPH and ABTS bioassays, respectively. The
presence of naphthyl, benzhydryl, benzoyl, furoyl and heterocyclic rings on the piperazine system was essential to exert anticipated
cytotoxic effects against cancer cell lines. The structure of the final compounds was adequately confirmed via spectroscopic techniques,
elemental analysis analysis and characterization of physical properties.
Keywords: Berberine, piperazine, piperidine, carbazole, morpholine, antioxidant, cytotoxicity, cervical cancer, DPPH assay, ABTS assay.
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