RETENTION BEHAVIOR AND BIOLOGICAL ACTIVITY OF N-SUBSTITUTED-2-PHENYLACETAMIDE DERIVATES
DOI:
https://doi.org/10.7251/COMEN1401124VAbstract
Phenylacetamide derivatives are a group of compounds that exhibit a wide range of biological activities as analgetic, anticonvulsant, pesticide, cytostatic. It is well known that the biological activity and the field of activity of the substance are greatly dependent on its physical, chemical and structural properties. In this paper, we applied QSRR analysis (Quantitative Structure Retention Relationships), which is based on the prediction of biological properties of compounds based on their chromatographic retention behaviors. To that end, retention constants of investigated N-substituted-2-phenylacetamide were determined by reversed phase thin-layer chromatography, (HPTLC RP18 F254s) in the presence of different volume fractions of n-propanol and tetrahydrofuran. The resulting data were correlated with molecular descriptors determined in different ways in order to establish the mathematical model that describes the relationship between retention properties and biological activities of investigated phenylacetamides.
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[3] D. Kadadevar, K. C. Chaluvaraju, M. S. Niranjan, C. Sultanpur, S. K. Madinur, Nagaraj, M. Hegde, M. Smitha, K. Chakraborty, Synthesis of N-(substituted phenyl)-2 [5- phenyl-2H-1, 2, 4-triazol-3ylamino] acetamide as anticonvulsant, International Journal of Chem.Tech. Research, Vol. 3 (2011) 1064−1069.
[4] M. Haramoto, H. Yamanaka, H. Sano, S. Sano, H. Otani, Fungicidal activities of cyflufenamid against various plant-pathogenic fungi, Journal of Pesticide Science, Vol. 31 (2006) 95−101.
[5] H. H. Li, Z. J. Wang, L. Z. Wang, Z. M. Li, W. G. Zhao, Syntheses and biological activities of α-substitued phenylethyl amide compounds, Chemical Journal of Chinese Universities, Vol. 32 (2011) 79−83.
[6] S. I. Kovalenko, I. S. Nosulenko, Y. Alexey, G. G. Berest, L. N. Antypenko, A. N. Antypen-ko, A. M. Katsev, Substituted 2-[(2-Oxo-2H-[1, 2, 4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with thiazole and thiadiazole fragments: Synthesis, physicochemical properties, cytotoxicity, and anticancer activity, Science Pharmaceutica, Vol. 80 (2012) 837−865.
[7] O. Chahrour, A. Abdalla, F. Lam, C. Midgley, S. Wang, Synthesis and biological evaluation of benzyl styrylsulfonyl derivatives as potent anticancer mitotic inhibitors, Bioorganic and Medicinal Chemistry Letters, Vol. 21 (2011) 3066−3069.
[8] N. R. Modi, R. J. Shah, M. J. Patel, M. Suthar, B. F. Chauhan, L. J. Patel, Design, synthesis, and QSAR study of novel 2-(2,3-dioxo-2,3- dihydro-1H-indol-1-yl)-N-phenylacetamide derivatives as cytotoxic agents, Medicinal Chemistry Research, Vol. 20 (2011) 615−625.
[9] R. Todeschini, V. Consonni, Handbook of molecular Descriptors, Wiley-VHC, Weinhem, 2000.
[10] S. Gocan, F. Irimie, G. Cimpan, Prediction of the lipophilicity of some plant growth-stimulating amido esters of ethanolamine using reversed-phase thin-layer chromatography, Journal of Chromatography A, Vol. 675 (1994) 282−285.
[11] N. Perišić-Janjić, G. Vastag, J. Tomić, S. Petrović, Effect of the physicochemical properties of N,N-disubstituted-2- phenylacetamide derivatives on their retention behavior in RP-TLC, Journal of Planar Chromatography - Modern TLC, Vol. 20 (2007) 353−359.
[12] Dj. Vaštag, N. Perišić-Janjić, J. Tomić, S. Petrović, Evaluation of the lipophilicity and pre-diction of biological activity of some N-cyclohexyl-N-substituted-2-phenylacetamide derivatives using RP-TLC, Journal of Planar Chromatography Modern TLC, Vol. 24 (2011) 435−440.
[13] http://www.vcclab.org Accessed May 2011.
[14] C. Sârbu, K. Kuhajda, S. Kevresan, Evaluation of the lipophilicity of bile acids and their derivatives by thin-layer chromatography and principal component analysis, Journal of Chromatogra-phy A, Vol. 917 (2001) 361–366.
[15] C. Sârbu, T. Djaković-Sekulić, N. Perišić-Janjić, Evaluation of lipophilicity of some benzimidazole and benztriazole derivatives by RP HPTLC and PCA, Journal of Pharmaceutical and Biomedical Analysis, Vol. 30 (2002) 739−745.
[16] T. Djaković-Sekulić, A. Smolinski, N. Perišić-Janjić, M. Janicka, Chemometric characterization of (chromatographic) lipophilicity parameters of newly synthesized s-triazine derivatives, Journal of Chemometrics, Vol. 22 (2008) 195−202.
[17] L. Komsta, R. Skibinski, A. Berecka, A. Gumieniczek, B. Radkiewicz, M. Radon, Revisiting thin-layer chromatography as a lipophilicity determination tool-A comparative study on several tech-niques with a model solute set, Journal of Pharmaceutical and Biomedical Analysis, Vol. 53 (2010) 911−918.
[18] Gy. Vastag, S. Apostolov, N. Perišić-Janjić, B. Matijević, Multivariate analysis of chromatographic retention data and lipophilicity of phenylacetamide derivatives, Analytica Chimica Acta, Vol. 767 (2013) 44−49.
[19] E. Csomós, K. Héberger, L. Simon-Sarkadi, Principal component analysis of biogenic amines and polyphenols in Hungarian wines, Journal of Agricultural and Food Chemistry, Vol. 50 (2002) 3768−3774.
[20] E. R. Malinowski, Factor Analysis in Chemistry, 2nd edn, chap. 9, Chromatography, Wiley-Interscience, New York 1991, 266−291.
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2014-09-26
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