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LogP values of 41 biologically active chalcones (Figure 1, 1) and their cyclic analogs, E-2-(X-benzylidene)-1-indanones (Figure 1, 2), -tetralones (Figure 1, 3) and -benzosuberones (Figure 1, 4) have been determined by an optimized and validated RPTLC method. The optimized RPTLC investigations were performed on silanized silica gel 60F254 as stationary phase with methanol–water, 60 + 40 (v/v) as mobile phase. The RPTLC method was validated by analysis of three drugs, diazepam, progesterone, and PGE1 ethyl ester, with known experimental logP values. The calibration equation used for the logP TLC calculations was: logP = 4.315RM + 1.436 (n = 11, r = 0.996, s = 0.02, F = 1089). On the basis of the logP TLC values obtained structure–lipophilicity relationships for the investigated chalcones (1) and cyclic chalcone analogs (2–4) were studied. The effects of ring closure, ring size, and the nature and the position of the aromatic substituents on the logP TLC values of the compounds are discussed.

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