Publication: Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines
Issued Date
2013-08-01
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ISSN
15548120
10542523
10542523
Other identifier(s)
2-s2.0-84879501042
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Mahidol University
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SCOPUS
Bibliographic Citation
Medicinal Chemistry Research. Vol.22, No.8 (2013), 4016-4029
Suggested Citation
Ratchanok Pingaew, Pan Tongraung, Apilak Worachartcheewan, Chanin Nantasenamat, Supaluk Prachayasittikul, Somsak Ruchirawat, Virapong Prachayasittikul Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines. Medicinal Chemistry Research. Vol.22, No.8 (2013), 4016-4029. doi:10.1007/s00044-012-0402-6 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31520
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Title
Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines
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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.