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Title: Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines
Authors: Ratchanok Pingaew
Pan Tongraung
Apilak Worachartcheewan
Chanin Nantasenamat
Supaluk Prachayasittikul
Somsak Ruchirawat
Virapong Prachayasittikul
Srinakharinwirot University
Mahidol University
Chulabhorn Research Institute
Keywords: Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 1-Aug-2013
Citation: Medicinal Chemistry Research. Vol.22, No.8 (2013), 4016-4029
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 IC50value 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 EHOMO(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.
ISSN: 15548120
Appears in Collections:Scopus 2011-2015

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