Journal : Acta Chromatographica
Article : Reversed-phase TLC study of the lipophilicity of some 3-hydroxy-1,2-benzisoxazoles substituted in the benzene ring

Authors :
Dejaegher, B.
Vrije Universiteit Brussel — VUB Analytical Chemistry and Pharmaceutical Technology (FABI), Pharmaceutical Institute Laarbeeklaan 103 1090 Brussels Belgium,
Vander Heyden, Y.
Vrije Universiteit Brussel — VUB Analytical Chemistry and Pharmaceutical Technology (FABI), Pharmaceutical Institute Laarbeeklaan 103 1090 Brussels Belgium, yvanvdh@vub.ac.be,
Durón, R. R.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Almaguer, L. C.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Garza-Juárez, A.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Salazar Cavazos, M. L.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México,
Waksman de Torres, N.
Universidad Autónoma de Nuevo León Departamento de Química Analítica, Facultad de Medicina P.O. Box 2316 Sucursal Tecnológico 64841 Monterrey Nuevo León México, nwaksman@fm.uanl.mx,
Garza-Juárez, A.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Waksman de Torres, N.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Salazar Cavazos, M. L.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México, masalaz52@yahoo.com,
Durón, R. R.
UANL, México Department of Analytical Chemistry, Facultad de Medicina Maderoy Aguirre Pequeño Col. Mitras Centro C.P. 64460 Mty, N.L. México,
Briciu, R. D.
Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania,
Kot-Wasik, A.
Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland,
Namieśnik, J.
Gdańsk University of Technology Chemical Faculty Narutowicza Str. No 11/12 80-952 Gdańsk Poland,
Sârbu, C.
Babeş-Bolyai University Faculty of Chemistry and Chemical Engineering Arany Janos Str. No 11 RO-400028 Cluj Napoca Romania, costelsrb@yahoo.co.uk,
Sławik, T.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Skibiński, R.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland, robert.skibinski@am.lublin.pl,
Paw, B.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Działo, G.
Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland,
Abstract : The relative lipophilicity, RM0, 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 RM0was compared with computed partition coefficients IAlogP, A logP s , clogP, milogP, logP KOWIN , and xlogP. The best correlation ( r > 0.9) was found between RM0and logP KOWIN and xlogP values. Principal-components analysis (PCA) was also used to compare RM0values 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 RM0values for both groups of compounds were in accor-dance with the equation RM0aRM0+b(r> 0.9).

Keywords : lipophilicity, RP-TLC, retention RM0, calculated partition coefficients, 3-hydroxy-1,2-benzisoxazoles, 1,2-benzisothiazolones,
Publishing house : University of Silesia in Katowice
Publication date : 2009
Number : Vol. 21, no. 2
Page : 251 – 258

Bibliography
: 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)
DOI :
Qute : Dejaegher, B. ,Vander Heyden, Y. ,Durón, R. R. ,Almaguer, L. C. ,Garza-Juárez, A. ,Salazar Cavazos, M. L. ,Waksman de Torres, N. ,Garza-Juárez, A. ,Waksman de Torres, N. ,Salazar Cavazos, M. L. ,Durón, R. R. ,Briciu, R. D. ,Kot-Wasik, A. ,Namieśnik, J. ,Sârbu, C. ,Sławik, T. ,Skibiński, R. ,Paw, B. ,Działo, G. ,Działo, G. , Reversed-phase TLC study of the lipophilicity of some 3-hydroxy-1,2-benzisoxazoles substituted in the benzene ring. Acta Chromatographica Vol. 21, no. 2/2009
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