RP-HPLC OF NEW ANTIDEPRESSANT 2-AMINO-2-OXAZOLINES - A COMPARATIVE-STUDY OF THEIR LIPOPHILICITY

A comparative study of lipophilicity in a series of 5-(1-aryl-4-piperazino)methyl-2-amino-2-oxazolines with antidepressant activity has been carried out using a RP-HPLC technique. This chromatographic method allowed the determination of log k(w)' values through extrapolation to 100% water from capacity factors data. The partition coefficients (log P(o/w)) and ionization constants (pK(a)) were measured by classical methods. A good correlation between log P(o/w) and log k(w)' was found, confirming the feasibility of using the latter as a lipophilicity descriptor. In this homogeneous chemical series the nature and the position of the substituents on the aromatic ring did not induce important variations on the pK(a) values, whereas they accounted for a great part in lipophilicity data.