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Reversed-phase TLC study of the lipophilicity of some 3-hydroxy-1,2-benzisoxazoles substituted in the benzene ring

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The relative lipophilicity, R M0 , and specific hydrophobic surface area of eleven 3-hydroxy-1,2-benzoisoxazoles substituted in the benzene ring (two isomeric fluoro, three isomeric chloro, three isomeric bromo and dibromo derivatives, and a nitro derivative) have been studied by reversed-phase thin layer chromatography (RP-TLC) on silica gel RP-C18 plates with methanol-water mixtures as mobile phases. Linear correlation between the volume fraction of methanol and R M values over a limited range was established with high correlation coefficients ( r > 0.99). Lipophilicity R M0 was compared with computed partition coefficients IAlogP, A logP s , clogP, milogP, logP KOWIN , and xlogP. The best correlation ( r > 0.9) was found between R M0 and logP KOWIN and xlogP values. Principal-components analysis (PCA) was also used to compare R M0 values with computed partition coefficients. The chromatographic behaviour of 3-hydroxy-1,2-benzisoxazoles was compared with that of their bioisosteric analogues 1,2-benzisot-iazolonoles. Experimental R M0 values for both groups of compounds were in accor-dance with the equation R M0 aR M0 +b(r> 0.9).
Rocznik
Strony
251--258
Opis fizyczny
Bibliogr. 27 poz., rys., tab.
Twórcy
autor
  • Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland
  • Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland, robert.skibinski@am.lublin.pl
autor
  • Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland
autor
  • Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland
Bibliografia
  • [1] Leo, C. Hansch, D. Elkins, Chem. Rev., 71 , 525, (1971)
  • [2] T. Fujita, J. Iwasa, C. Hansch, J. Am. Chem Soc., 86 , 5175, (1964)
  • [3] R. F. Rekker, R. Mannhold, Calculation of Drug Lipophilicity, The Hydrophobic Fragmental Constant Approach VCH, Weinheim, 1992
  • [4] L. G. Danielsson, Y. H. Zhang, Trends Anal. Chem., 15 , 188, (1996)
  • [5] T. Hartmann, J. Schmitt, Drug Discovery Today, Technologies, 1 , 431, (2004)
  • [6] M. E. Morgan, L. Kui, B. Anderson, J. Pharm. Sci, 87 , 238, (1998)
  • [7] A. Persona, Z. Fekner, B. Marczewska, T. Sławik, XLV Conference of Polish Chemical Society vol II 870, Kraków, (2002)
  • [8] G. Bouchard, P. A. Carrupt, B. Testa. V. Gobry, H. H. Girault, Chem Eur. J., 8 , 3478, (2002)
  • [9] J. Østergaard, S. H. Hansen, H. Larsen, Ch. Shou, N. H. H. Heegard, Electrophoresis, 24 , 1078, (2003)
  • [10] M. Bajda, A. Bucki, J. Szlęk, M. Szwaczkiewicz, M. Świerczek, B. Malawska, Biomed. Chromatogr. DOJ: 10.1002/bmc (2007)
  • [11] T. Bączek, M. Markuszewski, R. Kaliszan, M. A. van Straten, H. A. Claessens; J. High Resol. Chromatogr., 23 , 667, (2000)
  • [12] J. Kresta, P. Kastner, J. Klimeš, V. Klimešowa, J. Liq. Chromatogr. Rel. Technolog., 27 , 2539, (2004)
  • [13] D. Matosiuk, K. Jóźwiak, J. Planar Chromatogr., 13 , 130, (2000)
  • [14] S. Boryczka, K. Kulig, B. Malawska, J. Planar Chromatogr., 16, 117, (2003)
  • [15] K. Kulig, B. Malawska, Biomed. Chromatogr., 17 , 1, (2003)
  • [16] T. Sławik, B. Paw, J. Planar Chromatogr., 16, 442, (2003)
  • [17] I. V. Tetko, V. J. Tanchuk, VCC — Lab, 2002, http://146.107.217.178/servlets/vcc.lab?action-alogps
  • [18] C. Bertaccini, M. Impiccatore, T. Vitali, Pharmacol. Res. Commun., 3 , 385, (1971); Chem. Abstr., 77 , 70117, (1972)
  • [19] M. Impiccatore, T. Vitali, G. Bertaccini, Boll. Soc. Ital. Biol. Sper., 47 , 296, (1971); Chem. Abstr., 76 , 254, (1972)
  • [20] H. Böshagen, Chem. Ber., 100 , 954, (1967)
  • [21] T. Sławik, E. Domagalina, Acta Polon. Pharm., XLI, 625, (1984)
  • [22] T. Braumann, J. Chromatogr., 323, 191, (1986)
  • [23] K. Dross, R. F. Rekker, G. de Viers, R. Mannhold, Quant. Struct. Act. Relat., 17 , 549, (1998)
  • [24] P. Kästern, L. Klime<, P. Velenovska, V. Klime15 , 200, (2002)
  • [25] A. Pyka, M. Dołowy, J. Liq. Chromatogr. Rel. Technol., 28 , 293, (2005)
  • [26] T. Sławik, C. Kowalski, J. Chromatogr. A, 952 , 295, (2002)
  • [27] M. Daszykowski, B. Walczak, D.L. Massart, Chemom. Intell. Lab. Syst. 65 , 97, (2003)
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-a90bc98e-478b-43c1-b2ec-da16ea12d87e
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