Design, synthesis and cytotoxicity of novel N-benzylpiperidin-4-one oximes on human cervical cancer cells

A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Additionally, single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymm...

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Bibliographic Details
Published in:	Journal of chemical sciences (Bangalore, India) Vol. 126; no. 3; pp. 861 - 873
Main Authors:	DINDULKAR, SOMESHWAR D, BHATNAGAR, IRA, GAWADE, RUPESH L, PURANIK, VEDAVATI G, KIM, SE-KWON, ANH, DONG HYUN, PARTHIBAN, PARAMASIVAM, JEONG, YEON TAE
Format:	Journal Article
Language:	English
Published:	India Springer India 01-05-2014
Subjects:	Chemistry Chemistry and Materials Science Chemistry/Food Science HeLa cells N-benzylpiperidin-4-one oximes single-crystal XRD cytotoxicity
Online Access:	Get full text
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Summary:	A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Additionally, single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymmetrical ketones existed as E-isomer as witnessed by their NMR and XRD data. Among the synthesized target compounds that evaluated for their in vitro cytotoxicity against human cervical carcinoma (HeLa) cells, five compounds were potent with IC 50 < 17 μ M. 1-Benzyl-2,6- bis (4-isopropylphenyl)-3-methylpiperidin-4-one oxime 3c with an IC 50 of 13.88 μ M was found to be the best active compound as depicted by the microscopic analysis. Graphical Abstract A series of fifteen diversified N-benzylpiperidin-4-one oximes were synthesized and characterized by their NMR spectral data. Single-crystal XRD analysis was performed for the representative symmetrically and unsymmetrically substituted molecules. All the synthesized oximes from unsymmetrical ketones existed as Eisomer. Among the synthesized target compounds that were evaluated for in vitro cytotoxicity against human cervical carcinoma (HeLa) cells, 1-benzyl-2,6- bis (4-isopropylphenyl)-3-methylpiperidin-4-one oxime with an IC 50 of 13.88 μ M was most potent.
ISSN:	0974-3626 0973-7103
DOI:	10.1007/s12039-014-0622-z