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|Title:||Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines|
Multiple linear regression
cancer cell culture
carbon nuclear magnetic resonance
cell strain HepG2
proton nuclear magnetic resonance
quantitative structure activity relation
|Abstract:||Simplified 1,3-disubstituted urea derivatives (11-24) of phenylethylamines, homoveratylamines, 2-pyridylethylamines, 2-picolylamines as well as xylylenediamines were synthesized and investigated for their cytotoxic activities. The results revealed that most analogs displayed cytotoxicity against HepG2 and MOLT-3 cell lines. The bis-thiourea derivatives 23 and 24 exhibited higher inhibitory potency against HepG2 cell than the reference drug, etoposide. 1,1′-(1,3-phenylenebis(methylene))bis(3-(4-chlorophenyl) thiourea) 24 was shown to be the most potent cytotoxic compound against MOLT-3 cell line with an IC50 value of 1.62 μM. QSAR studies suggested that compounds with high ionization potential displayed high cytotoxicity against HuCCA-1 cell line. Furthermore, derivatives with dimethoxyphenyl group had high radial distribution function with a correspondingly high cytotoxicity against A549 cell line. Moreover, analogs 23 and 24 had low values of E HOMO (energy of the highest occupied molecular orbital energy) as well as high cytotoxicity against HepG2 cell line. This study affords an easily accessible approach for the synthesis of promising anticancer agents. The developed QSAR models provided pertinent information into the physicochemical properties governing the investigated biologic properties. © 2012 Springer Science+Business Media New York.|
|Appears in Collections:||Scopus 1983-2021|
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