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

• Autorzy: Sławik T. , Skibiński R. , Paw B. , Działo G
• 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).

Słowa kluczowe

EN

lipophilicity; RP-TLC; retention RM0; calculated partition coefficients; 3-hydroxy-1,2-benzisoxazoles; 1,2-benzisothiazolones

• Wydawca: University of Silesia in Katowice ; Akademiai Kiado
• Czasopismo: Acta Chromatographica
• Rocznik: 2009
• Tom: Vol. 21, no. 2
• Strony: 251--258
• Opis fizyczny: Bibliogr. 27 poz., rys., tab.

Twórcy

autor

Sławik T.

• Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland

autor

Skibiński R.

• Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland

autor

Paw B.

• Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland

autor

Działo G

• Medical University of Lublin Department of Medicinal Chemistry, Pharmaceutical Faculty Jaczewskiego 4 20-090 Lublin Poland

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