Publication: Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines
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Issued Date
2013
Resource Type
File Type
application/pdf
ISSN
10542523
Other identifier(s)
2-s2.0-84879501042
Rights Holder(s)
Scopus
Bibliographic Citation
Medicinal Chemistry Research. Vol 22, No.8 (2013), p.4016-4029
Suggested Citation
Pingaew R., Tongraung P., Worachartcheewan A., Nantasenamat C., Prachayasittikul S., Ruchirawat S., Prachayasittikul V. Cytotoxicity and QSAR study of (thio)ureas derived from phenylalkylamines and pyridylalkylamines. Medicinal Chemistry Research. Vol 22, No.8 (2013), p.4016-4029. doi:10.1007/s00044-012-0402-6 Retrieved from: https://hdl.handle.net/20.500.14740/6604
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.
Subject(s)
Anticancer
Multiple linear regression
QSAR
Urea
Aliphatic amine
Antineoplastic agent
Doxorubicin
Etoposide
Homoveratylamine derivative
Phenylalkylamine
Thiourea derivative
Unclassified drug
Xylylenediamine derivative
Article
Cancer cell culture
Carbon nuclear magnetic resonance
Cell strain HepG2
Controlled study
Cytotoxicity
Drug potency
Drug synthesis
Human
Human cell
Ionization
Proton nuclear magnetic resonance
Quantitative structure activity relation
Quantum chemistry
Multiple linear regression
QSAR
Urea
Aliphatic amine
Antineoplastic agent
Doxorubicin
Etoposide
Homoveratylamine derivative
Phenylalkylamine
Thiourea derivative
Unclassified drug
Xylylenediamine derivative
Article
Cancer cell culture
Carbon nuclear magnetic resonance
Cell strain HepG2
Controlled study
Cytotoxicity
Drug potency
Drug synthesis
Human
Human cell
Ionization
Proton nuclear magnetic resonance
Quantitative structure activity relation
Quantum chemistry