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pH-partition profiles of 4-(3-oxo-1,2-benzisothiazolin-2-yl)phenyl and phenoxyalkanoic acids. 2003

Claudia Silva, and Marco Mor, and Federica Vacondio, and Valentina Zuliani, and Pier Vincenzo Plazzi
Dipartimento Farmaceutico, Università degli Studi di Parma, Parco Area delle Scienze 27/a, I-43100 Parma, Italy.

The 1,2-benzisothiazolin-3-one nucleus is well known in the medicinal chemistry literature for the variety of biological effects exerted by its derivatives. In the present paper, the dependence of the n-octanol/buffer distribution coefficient (D) on pH of four 4-(3-oxo-1,2-benzisothiazolin-2-yl)phenyl and phenoxyalkanoic acids was investigated, employing the reference shake-flask method. From the analysis of the pH-partition profiles in the chosen partition system, the logP(AH), the logP(A(-)) and the pK(a) values for each compound were determined. The physico-chemical data obtained were compared to the pK(a) and logP values of the corresponding phenyl and phenoxyalkanoic acids, and an estimation of the lipophilic and electronic contribution of the 1,2-benzisothiazolin-3-one substituent in the para-position is proposed. The 1,2-benzisothiazolin-3-one nucleus behaves as a lipophilic, moderately electron-withdrawing group.

UI MeSH Term Description Entries
D002021 Buffers A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. Buffer
D002626 Chemistry, Pharmaceutical Chemistry dealing with the composition and preparation of agents having PHARMACOLOGIC ACTIONS or diagnostic use. Medicinal Chemistry,Chemistry, Pharmaceutic,Pharmaceutic Chemistry,Pharmaceutical Chemistry,Chemistry, Medicinal
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D006880 Hydroxy Acids Organic compounds containing both the hydroxyl and carboxyl radicals. Hydroxy Acid,Acid, Hydroxy,Acids, Hydroxy
D013844 Thiazoles Heterocyclic compounds where the ring system is composed of three CARBON atoms, a SULFUR and NITROGEN atoms. Thiazole
D020003 1-Octanol A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) n-Octanol,n-Octyl Alcohol,1 Octanol,Alcohol, n-Octyl,n Octanol,n Octyl Alcohol

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